6-Phenylnicotinic acid → HCID 57682708, compound

HRID 494232Notes

Reaction equation

HRID 494232 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2C(=O)C(F)(F)F)=[C:4]([Cl:18])[CH:3]=1.[C:19]1([C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][N:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[Cl:18][C:4]1[CH:3]=[C:2]([NH:1][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:26][CH:27]=2)[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][NH:9]2

Participants

3

Reactant 2

HCID 1201186-Phenylnicotinic acidHCID 86605997HCID 86605997, compound

Product 1

HCID 57682708HCID 57682708, compound

Procedure

Using the procedure outlined in Example 38, the title compound was prepared from 7-amino-5-chloro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D104) (50 mg, 0.251 mmol) and 6-phenyl nicotinic acid (60 mg, 0.302 mmol) as a white solid (55 mg). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.11 (s, 1H), 8.22 (dd, 1H), 8.05 (dd, 1H), 7.85 (d, 1H), 7.65 (br-s, 1H), 7.45-7.55 (m, 3H), 7.00 (br.s, 1H), 6.79 (d, 1H), 4.10 (br-s, 1H), 3.25-3.30 (m, 2H), 2.75-2.80 (m, 2H), 1.95-2.00 (m, 1H), 1.57 (s, 6H). MS(ES): MH+ 364.

Sources & evidence

ORD record
ord-3f889d5229914ac1923e32248ffd3da0
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

Loading…