2-Aminoadamantane-2-carboxylic acid

5-(2, 6-Dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acid (2) was heated under reflux in SOCl2 for 2 h followed by cooling and concentration in vacuo. The residue was then dissolved in toluene and evaporated (3*) to remove HCl. The residue was then taken up in dry THF and added to a well agitated mixture of 5:1 THF/water (15 mL/g of acid chloride) containing 1.1 equiv 2-aminoadamantane-carboxylic acid and 2.2 equiv of NaOH at 5 C. Following the addition, the stirring was continued for 18 h at ambient temp. After this time, the mixture is made acidic with 1 N HCl and extracted (3*) with CH2Cl2, dried over sodium sulfate and evaporated. The residue was chromatographed using a 0-15% CH2Cl2/MeOH gradient. Evaporation provided the title compound 26. 71% yield; off-white solid; 1H NMR (CDCl3) delta 7.20-7.36 (m, 4H), 6.90-7.04 (m, 3H), 6.51 (d, J = 8.5 Hz, 2H), 3.54-3.63 (m, 6H), 2.71-2.81 (m, 2H), 2.23 (d, J = 12.8 Hz, 2H), 2.07 (d, J = 12.2 Hz, 2H), 1.68-1.95 (m, 8H). MS (ESI) m/z: Calcd for C29H30FN3O5 519.22 [M]+, found 518.9 [M-H]-.Following the method of Quere- 30 was obtained from 5-(2, 6-dimethoxyphenyl)-l-(4-fluorophenyl)-lH- pyrazole-3-carboxylic acid (Hi) and Carboxylic acid (XV) (287 mg, 0.260 mmol) was dissolved in dry NMP (3.7 ml). HATU (98.7 mg, 0.260 mmol, 1.0 eq.) was added as solid and to this mixture DIPEA (89 mul, 0.52 mmol, 2.0 eq.) was added. After stirring for 5 min this solution was transferred within 5 min to a suspension of Carboxylic acid of formula (XV) (287 mg, 0.260 mmol) was dissolved in dry NMP (3.7 ml). HATU (98.7 mg, 0.260 mmol, 1.0 eq.) was added as solid and to this mixture DIPEA (89 mu, 0.52 mmol, 2.0 eq.) was added. After stirring for 5 min this solution was transferred within 5 min to a suspension of Carboxylic acid (XII) (248 mg, 0.222 mmol) was dissolved in dry NMP (3 ml). HATU (84.3 mg, 0.222 mmol, 1.0 eq.) was added as solid and to this mixture DIPEA (76 mul, 0.443 mmol, 2.0 eq.) was added. After stirring for 5 min this solution was transferred within 5 min to a suspension of

Molecular Weight:195.26
XLogP3:-1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:195.125928785
Monoisotopic Mass:195.125928785
Topological Polar Surface Area:63.3
Heavy Atom Count:14
Complexity:259
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes