4-AMINO-2-BROMOQUINOLINE

Compound 5 was prepared by a method described elsewhere [Kornblum, N. et al. The reduction of optically active 2-nitrooctane and α-phenylnitroethane. J Am. Chem. Soc. 1955. 77. 6266-6269; Den Hertog, H. J.; Buurman, D. J. Rec. Trav. Chim. des Pays-Bas. 1972, 91, 841-849]. In brief, compound 4 (1.82 g, 7.2 mmol) was dissolved in acetic acid. Iron powder (5 eq) was added and the reaction stirred at 65 Compound 5 was prepared by a method described elsewhere [Kornblum, N. et al. The reduction of optically active 2-nitrooctane and alpha-phenylnitroethane. J Am. Chem. Soc. 1955. 77. 6266-6269; Den Hertog, H. J.; Buurman, D. J. Rec. Trav. Chim. des Pays-Bas. 1972, 91, 841-849]. In brief, compound 4 (1.82 g, 7.2 mmol) was dissolved in acetic acid. Iron powder (5 eq) was added and the reaction stirred at 65 0C for 2.5 hours. The iron powder was filtered off, washed with DCM. pH was adjusted to 9 with 2M NaOH. This was filtered again and the residue was washed with ammonia. The aqueous layer was extracted with DCM, dried on MgSO4 and evaporated. The product was purified by column chromatography, eluent DCM. Yield: 0.69 g (43%). 1H NMR (CDCl3) delta 4.81 (bs, 2H, NH2), 6.76 (s, IH, Ar), 7.48 (t, IH5 J = 7.3I5 7.06 Hz5 Ar)5 7.62-7.73 (m5 2H, Ar), 7.94 (d, IH5 J= 8.76 Hz, Ar). 13C NMR (CDCl3) delta 106.6O5 117.82, 120.21, 125.37, 129.19, 130.4O5 142.59, 148.78, 150.90.In brief, compound 5 (0.32 g, 1.40 mmol) was dissolved in pyridine (5 mL) and cyclopenthanecarbonyl chloride (1.3 eq) was added. The reaction stirred at 115 0C for 2 hours. After the reaction was completed, pyridine was evaporated. The product was purified by column chromatography, eluent 5% MeOH in DCM. The product was crystallized from MeOH to give white crystals. Yield: 0.35 g (79%). MS (ESI) m/z: 319.9 [M+Hf1, [M-H]+1. 1H NMR (CDCl3) delta 1.64-2.07 (m, 8H, 4CH2), 2.53-3.00 (m, IH, CH), 7.54-7.62 (m, IH, Ar), 7.69-7.79 (m, 2H, Ai'), 7.92 (bs, IH, NH), 7.99-8.08 (m, IH, Ar), 8.43 (s, IH, Ar). 13C NMR (CDCl3) delta 25.96, 30.51, 47.2, 114.51, 118.85, 126.76, 129.89, 130.40, 141.56, 143.17, 148.63, 175.07 [Chang, L. C. W. et al. 2, 4, 6- Trisubstituted pyrimidines as a new class of selective adenosine A1 receptor antagonists, J. Med. Chem. 2004, 47, 6529-6540].

Molecular Weight:223.07
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:221.97926
Monoisotopic Mass:221.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes