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

HRID 1159911Notes

Reaction equation

HRID 1159911 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.Cl[C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1>>[CH2:2]1[C:41]2[C:35](=[CH:36][CH:37]=[C:38]([NH:39][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:40]=2)[CH2:5][CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 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 4-chloroaniline by a procedure similar to Example 27, Step D. 1H NMR (400 MHz, DMSO-d6) δ 6.67 (d, 1H, J=5.2 Hz), 7.18 (t, 1H, J=7.0 Hz), 7.26-7.32 (m, 4H), 7.38 (d, 1H, J=7.7 Hz), 7.49-7.66 (m, 4H), 7.73 (d, 1H, J=8.9 Hz), 7.84 (d, 1H, J=8.7 Hz), 8.06 (s, 1H), 8.35 (d, 1H, J=5.4 Hz), 8.45 (d, 1H, J=8.9 Hz), 8.90 (d, 1H, J=6.8 Hz), 9.79 (s, 1H), 10.98 (s, 1H); ESIMS (M+H)+=553.

Sources & evidence

ORD record
ord-3a5617c2b07742ab919c39b0c5539c8c
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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