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

HRID 1159914Notes

Reaction equation

HRID 1159914 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][C:41]=1N1CCOCC1)[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 14853303-Fluoro-4-morpholinoanilineHCID 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-fluoro-4-(4-morpholinyl)aniline by a procedure similar to Example 64. 1H NMR (400 MHz, DMSO-d6) δ 2.97 (t, 4H, J=4.5 Hz), 3.76 (t, 4H, J=4.5 Hz), 6.61 (d, 1H, J=5.2 Hz), 6.96 (t, 1H, J=9.4 Hz), 7.17 (t, 1H, J=6.8 Hz), 7.29 (t, 2H, J=8.0 Hz), 7.37 (d, 2H, J=7.9 Hz), 7.48-7.55 (m, 2H), 7.63 (t, 1H, J=8.3 Hz), 7.73 (d, 1H, J=15.5 Hz), 7.85 (d, 1H, J=8.8 Hz), 8.06 (s, 1H), 8.32 (d, 1H, J=5.2 Hz), 8.47 (d, 1H, J=8.0 Hz), 8.90 (d, 1H, J=6.9 Hz), 9.63 (s, 1H), 10.97 (s, 1H); ESIMS (M+H)+=622.

Sources & evidence

ORD record
ord-2f98a69374cb4a92b09e573395e69dec
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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