4-Benzyloxyphenylacetic acid

White crystalline powder

2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-5-yl]acetamide A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (60 mg, 0.26 mmol), (4-benzyloxy-phenyl)-acetic acid (63 mg, 0.26 mmol), ethyldimethylpropylcarbodiimide hydrochloride (60 mg g, 0.31 mmol), N-hydroxybenzotriazole (42 mg, 0.31 mmol), and N-methyl morpholine (66 mg, 0.62 mmol) in 2 mL of DMF was shaken for 6 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.61 (m, 4H), 2.43 (m, 4H), 2.86 (t, 2H, J=6.78), 3.56 (s, 2H), 4.45 (t, 2H, J=6.78), 5.08 (s, 2H), 6.97 (m, 2H), 7.25-7.31 (m, 6H), 7.27 (m, 2H), 7.59 (m, 1H), 7.97 (s, 1H), 8.08 (s, 1H), 10.10 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.Example 17; 2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-5-yl]acetamide; A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (60 mg, 0.26 mmol), (4-benzyloxy-phenyl)-acetic acid (63 mg, 0.26 mmol), ethyldimethylpropylcarbodiimide hydrochloride (60 mg g, 0.31 mmol), N-hydroxybenzotriazole (42 mg, 0.31 mmol), and N-methyl morpholine (66 mg, 0.62 mmol) in 2 mL of DMF was shaken for 6 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.61 (m, 4H), 2.43 (m, 4H), 2.86 (t, 2H, J=6.78), 3.56 (s, 2H), 4.45 (t, 2H, J=6.78), 5.08 (s, 2H), 6.97 (m, 2H), 7.25-7.31 (m, 6H), 7.27 (m, 2H), 7.59 (m, 1H), 7.97 (s, 1H), 8.08 (s, 1H), 10.10 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.EXAMPLE 49 2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-yl]acetamide A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (48 mg, 0.21 mmol), (4-benzyloxy-phenyl)-acetic acid (50 mg, 0.21 mmol), ethyldimethylpropylcarbodiimide hydrochloride (47 mg g, 0.25 mmol), N-hydroxybenzotriazole (33 mg, 0.25 mmol), N-methyl morpholine (50 mg, 0.50 mmol) in 2 mL of DMF was shaken for 6 hours. The mixture was concentrated under reduced pressure, the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.82 (t, 2H, J=6.78), 3.60 (s, 2H), 4.38 (t, 2H, J=6.78), 5.09 (s, 2H), 6.97 (m, 2H), 7.11-7.45 (m, 8H), 7.65 (m, 1H), 7.93 (m, 1H), 8.12 (s, 1H), 10.27 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.Example 49; 2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-yl]acetamide; A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (48 mg, 0.21 mmol), (4-benzyloxy-phenyl)-acetic acid (50 mg, 0.21 mmol), ethyldimethylpropylcarbodiimide hydrochloride (47 mg g, 0.25 mmol), N-hydroxybenzotriazole (33 mg, 0.25 mmol), N-methyl morpholine (50 mg, 0.50 mmol) in 2 mL of DMF was shaken for 6 hours. The mixture was concentrated under reduced pressure, the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.82 (t, 2H, J=6.78), 3.60 (s, 2H), 4.38 (t, 2H, J=6.78), 5.09 (s, 2H), 6.97 (m, 2H), 7.11-7.45 (m, 8H), 7.65 (m, 1H), 7.93 (m, 1H), 8.12 (s, 1H), 10.27 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.EXAMPLE 3 2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide A mixture of Example 1C (42.0 mg, 0.183 mmol), (4-benzyloxy-phenylacetic acid (47.0 mg, 0.194 mmol), ethyldimethylpropylcarbodiimide hydrochloride (43.0 mg, 0.225 mmol), N-hydroxybenzotriazole (30.0 mg, 0.222 mmol), N-methyl morpholine (46.0 mg, 0.455 mmol) in 2 mL of DMF was shaken for 6 hour. The mixture was concentrated under reduced pressure and the residue dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/MeOH and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.66 (m, 4H), 2.49 (m, 4H), 2.91 (t, 2H, J=6.60), 3.76 (s, 2H), 4.42 (t, 2H, J=6.60), 5.14 (s, 2H), 7.03 (m, 2) 7.31-7.50 (m, 9H), 7.68 (m, 1H), 8.30 (s, 1H), 10.16 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide; A mixture of Example 1C (42.0 mg, 0.183 mmol), (4-benzyloxy-phenyl)-acetic acid (47.0 mg, 0.194 mmol), ethyldimethylpropylcarbodiimide hydrochloride (43.0 mg, 0.225 mmol), N-hydroxybenzotriazole (30.0 mg, 0.222 mmol), N-methyl morpholine (46.0 mg, 0.455 mmol) in 2 mL of DMF was shaken for 6 hour. The mixture was concentrated under reduced pressure and the residue dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/MeOH and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.66 (m, 4H), 2.49 (m, 4H), 2.91 (t, 2H, J=6.60), 3.76 (s, 2H), 4.42 (t, 2H, J=6.60), 5.14 (s, 2H), 7.03 (m, 2H), 7.31-7.50 (m, 9H), 7.68 (m, 1H), 8.30 (s, 1H), 10.16 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.A 10 mL culture tube with screw cap was charged with 2-(2-pyrrolidin-1-yl-ethyl)-2H-indazol-4-ylamine (56.0 mg, 0.243 mmol), (4-benzyloxy-phenyl)-acetic acid (60.0 mg, 0.248 mmol), ethyldimethylpropylcarbodiimide hydrochloride (57.0 mg, 0.298 mmol), N-hydroxybenzotriazole (40.0 mg, 0.296 mmol), N-methyl morpholine (64.0 mg, 0.633 mmol), 2 mL of N, N-dimethylformamide and the reaction vessel placed on a shaker for 6 hours. After this time, the N, N-dimethylformamide was removed in vacuo and the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.70 (m, 4H), 2.60 (m, 4H), 3.10 (s, 2H), 3.68 (s, 2H), 4.48 (t, 2H, J=6.44), 5.09 (s, 2H), 6.97 (m, 2H), 7.12-7.45 (m, 9H), 7.51 (m, 1H), 8.49 (s, 1H), 10.03 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.A 10 mL culture tube with screw cap was charged with 2-(2-pyrrolidin-1-yl-ethyl)-2H-indazol-4-ylamine (56.0 mg, 0.243 mmol), (4-benzyloxy-phenyl)-acetic acid (60.0 mg, 0.248 mmol), ethyldimethylpropylcarbodiimide hydrochloride (57.0 mg, 0.298 mmol), N-hydroxybenzotriazole (40.0 mg, 0.296 mmol), N-methyl morpholine (64.0 mg, 0.633 mmol), 2 mL of N, N-dimethylformamide and the reaction vessel placed on a shaker for 6 hours. After this time, the N, N-dimethylformamide was removed in vacuo and the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.70 (m, 4H), 2.60 (m, 4H), 3.10 (s, 2H), 3.68 (s, 2H), 4.48 (t, 2H, J=6.44), 5.09 (s, 2H), 6.97 (m, 2H), 7.12-7.45 (m, 9H), 7.51 (m, 1H), 8.49 (s, 1H), 10.03 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.

Molecular Weight:242.27
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:242.094294304
Monoisotopic Mass:242.094294304
Topological Polar Surface Area:46.5
Heavy Atom Count:18
Complexity:251
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes