1H-Imidazole-2-carboxylic acid → HCID 59631421, compound

HRID 1431689Notes

Reaction equation

HRID 1431689 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:7]2.[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[C:38](O)=[O:39]>>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:14][CH2:15][N:16]([C:38]([C:34]3[NH:33][CH:37]=[CH:36][N:35]=3)=[O:39])[CH2:17][CH2:18]1)=[N:7]2

Participants

3

Reactant 2

HCID 5743211H-Imidazole-2-carboxylic acidHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631421HCID 59631421, compound

Procedure

Prepared according to Procedure Q using 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine (40.0 mg, 0.09 mmol) and 1H-imidazole-2-carboxylic acid to give (4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazin-1-yl)(1H-imidazol-2-yl)methanone. 1H NMR (DMSO-d6) δ ppm 2.13 (br s, 3H), 3.06 (br s, 4H), 3.33-3.39 (m, 4H), 3.69 (br s, 4H), 3.84-3.85 (m, 2H), 4.66-4.69 (m, 2H), 6.50 (br s, 1H), 7.11-7.16 (m, 1H), 7.18-7.20 (m, 1H), 7.28-7.31 (m, 2H), 7.54 (br s, 1H), 7.79 (s, 1H), 8.38 (br s, 1H), 12.96 (s, 1H). Mass Spectrum (ESI) m/e=534.9 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ebe90975774946e580773e3d15c9cea5
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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