2,5-Difluorophenylacetic acid → 2-(2,5-Difluorophenyl)-N-(3-{3-[2-(phenylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)acetamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[CH2:38][C:39](O)=[O:40]>>[F:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[CH2:38][C:39]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:3]=1)=[O:40]Participants
3
Procedure
The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidine (see Example 3, Step H) and (2,5-difluorophenyl)acetic acid using the coupling conditions described in Example 5. 1H NMR (400 MHz, DMSO-d6): δ 3.76 (s, 2H), 6.53 (d, 1H, J=5.3 Hz), 6.94 (m, 1H), 7.10-7.27 (m, 7H), 7.41-7.48 (m, 2H), 7.69-7.76 (m, 3H), 7.89 (m, 1H), 8.27 (d, 1H, J=5.3 Hz), 8.48 (m, 1H), 8.83 (m, 1H), 9.56 (s, 1H), 10.39 (s, 1H). ES-LC/MS m/z=533 [M+H]+.
Sources & evidence
- ORD record
- ord-85e4af6e46814ad49455b6cf0321401f
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807673B2
Reaction notes
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