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

HRID 1159916Notes

Reaction equation

HRID 1159916 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.CN(C)CCO[C:39]1[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=1>>[CH2:2]1[C:40]2[C:39](=[CH:45][CH:44]=[C:42]([NH:43][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:41]=2)[CH2:5][CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 64846554-[2-(Dimethylamino)ethoxy]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-{[2-(dimethylamino)ethyl]oxy}aniline in a manner analogous to Example 64. 1H NMR (400 MHz, DMSO-d6) δ 2.30 (s, 6H), 2.71 (t, 2H, J=5.7 Hz), 4.05 (t, 2H, J=5.7 Hz), 6.54 (d, 1H, J=5.2 Hz), 6.87 (d, 2H, J=9.0 Hz), 7.15 (t, 1H, J=6.9 Hz), 7.29 (t, 2H, J=7.9 Hz), 7.37 (d, 1H, J=7.7 Hz), 7.47-7.66 (m, 5H), 7.86 (d, 1H, J=8.0 Hz), 8.04 (s, 1H), 8.26 (d, 1H, J=5.2 Hz), 8.46 (bd, 1H, J=8.9 Hz), 8.87 (d, 1H, J=6.9 Hz), 9.39 (s, 1H), 10.98 (s, 1H); ESIMS (M+H)+=606.

Sources & evidence

ORD record
ord-0d3b8094a8dc469c88273fad5f4b5fe2
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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