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

HRID 1159920Notes

Reaction equation

HRID 1159920 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.CO[C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][C:37]=1N1CCNCC1>>[CH2:2]1[C:37]2[C:36](=[CH:42][CH:41]=[C:39]([NH:40][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:38]=2)[CH2:5][CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 47388154-(Methyloxy)-3-(1-piperazinyl)anilineHCID 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-(methyloxy)-3-(1-piperazinyl)aniline in a manner analogous to Example 64. 1H NMR (400 MHz, DMSO-d6) δ 2.90 (s, 8H), 3.72 (s, 3H), 6.43 (d, 1H, J=5.3 Hz), 6.80 (d, 1H, J=8.8 Hz), 7.09 (t, 1H, J=6.5 Hz), 7.22 (d, 2H, J=8.1 Hz), 7.25 (d, 1H, J=3.9 Hz), 7.32 (t, 2H, J=8.3 Hz), 7.45 (q, 2H, J=7.9 Hz), 7.58 (quintet, 1H, J=8.3 Hz), 7.79 (d, 1H, J=8.2 Hz), 7.99 (s, 1H), 8.18 (d, 2H, J=5.7 Hz), 8.43 (bd, 1H, J=8.3 Hz), 8.81 (d, 1H, J=6.8 Hz), 9.26 (s, 1H), 10.92 (s, 1H); ESIMS (M+H)+=633.

Sources & evidence

ORD record
ord-ae1e907d865646fbbaabc8a09ce5667c
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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