2-Aminothiazole → N-(2',4'-difluoro-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1'-biphenyl]-3-yl) thiazol-2-amine

HRID 64168Notes

Reaction equation

HRID 64168 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]4[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=4)=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])[CH:7]=1.[S:31]1[CH:35]=[CH:34][N:33]=[C:32]1[NH2:36]>>[F:15][C:9]1[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=1[C:6]1[CH:5]=[C:4]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]4[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=4)=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:3]=[C:2]([NH:36][C:32]2[S:31][CH:35]=[CH:34][N:33]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 21552-AminothiazoleHCID 895010831-(5-bromo-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazole

Product 1

HCID 117777650N-(2',4'-difluoro-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1'-biphenyl]-3-yl) thiazol-2-amineYield 11.7%

Procedure

The compound was prepared from 1-(5-bromo-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazole (0.05 g, 0.107 mmol) using the procedure of Example 280 and thiazol-2-amine (0.01 g, 0.10 mmol, 1.0 eq.) to yield the title product in 11.7% yield (0.06 g). 1H NMR (400 MHz CD3OD): δ 9.45 (s, 1H), 8.39 (s, 1H), 8.11 (s, 1H), 8.01 (s, 1H), 7.94 (s, 1H), 7.86-7.83 (m, 2H), 7.74 (s, 1H), 7.67-7.65 (m, 1H), 7.45 (s, 1H), 7.28-7.27 (d, 1H), 7.16-7.11 (m, 2H), 6.89 (d, 1H), 3.95 (s, 3H) LC-MS (ESI): Calculated mass: 484.52; Observed mass: 485.2 [M+H]+ (rt: 1.01 min).

Sources & evidence

ORD record
ord-74f69e22f95144bab73031f84322d9a6
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

Loading…