3-Fluoroaniline → N-(3-{3-[2-(1,2,3,4-tetrahydro-7-isoquinolinylamino)-4-pyrimidinyl]-pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamide

HRID 1159923Notes

Reaction equation

HRID 1159923 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]4[C:30](F)=[CH:29][CH:28]=[CH:27][C:26]=4F)[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.F[C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38]>>[CH2:2]1[C:35]2[C:41](=[CH:40][CH:39]=[C:37]([NH:38][C:2]3[N:7]=[C:6]([C:8]4[C:9]([C:17]5[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=6)[CH:20]=[CH:21][CH:22]=5)=[N:10][N:11]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=45)[CH:5]=[CH:4][N:3]=3)[CH:36]=2)[CH2:5][CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

Product 1

HCID 59513880N-(3-{3-[2-(1,2,3,4-tetrahydro-7-isoquinolinylamino)-4-pyrimidinyl]-pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamide

Procedure

The title compound was prepared from N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide and 3-fluoroaniline in a manner analogous to Example 27, Step D. 1H NMR (400 MHz, DMSO-d6) δ 6.58 (d, 1H, J=5.3 Hz), 6.71 (m, 1H), 7.12 (m, 1H), 7.23 (m, 3H), 7.31 (d, 1H, J=7.7 Hz), 7.44 (m, 3H), 7.53 (m, 1H), 7.76 (m, 2H), 8.00 (s, 1H), 8.29 (d, 1H, J=5.3 Hz), 8.45 (d, 1H, J=9.0 Hz), 8.84 (d, 1H, J=7.0 Hz), 9.83 (s, 1H), 10.92 (s, 1H); ESIMS (M+H)+=537.

Sources & evidence

ORD record
ord-6d47f05b7cc64d57a73b3281f8d7d5a7
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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