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

HRID 1159918Notes

Reaction equation

HRID 1159918 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.C(N1CCN([C:42]2[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=2)CC1)C>>[CH2:2]1[C:43]2[C:42](=[CH:48][CH:47]=[C:45]([NH:46][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:44]=2)[CH2:5][CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 9367384-(4-Ethylpiperazin-1-yl)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-(4-ethyl-1-piperazinyl)aniline in a manner analogous to Example 64. 1H NMR (400 MHz, DMSO-d6) δ 1.07 (t, 3H, J=7.1 Hz), 2.40 (q, 2H, J=7.1 Hz), 2.53-2.57 (m, 4H overlapping with d6-DMSO), 3.08-3.11 (m, 4H), 6.52 (d, 1H, J=5.2 Hz), 6.86 (d, 2H, J=9.0 Hz), 7.15 (t, 1H, J=5.7 Hz), 7.29 (t, 2H, J=8.0 Hz), 7.36 (d, 1H, J=7.8 Hz), 7.46-7.54 (m, 4H), 7.62 (quintet, 1H, J=8.4 Hz), 7.85 (d, 1H, J=8.7 Hz), 8.04 (s, 1H), 8.25 (d, 1H, J=5.4 Hz), 8.47 (bd, 1H, J=8.9 Hz), 8.87 (d, 1H, J=6.9 Hz), 9.30 (s, 1H), 10.98 (s, 1H); ESIMS (M+H)+=631.

Sources & evidence

ORD record
ord-61405a3f331c4a109e6c3c0ad6e22a4f
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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