4-[2-(4-Methylpiperazin-1-yl)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 1159917Notes

Reaction equation

HRID 1159917 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.CN1CCN(CCO[C:44]2[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][CH:45]=2)CC1>>[CH2:2]1[C:45]2[C:44](=[CH:50][CH:49]=[C:47]([NH:48][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:46]=2)[CH2:5][CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 230087924-[2-(4-Methylpiperazin-1-yl)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-(4-methyl-1-piperazinyl)ethyl]oxy}aniline in a manner analogous to Example 64. 1H NMR (400 MHz, DMSO-d6) δ 2.11 (s, 3H), 2.20-2.35 (m, 4H), 2.62 (t, 2H, J=5.8 Hz), 3.00-3.60 (m, 4H overlapping with H2O), 3.98 (t, 2H, J=5.8 Hz), 6.47 (d, 1H, J=5.1 Hz), 6.80 (d, 2H, J=9.0 Hz), 7.08 (t, 1H, J=6.9 Hz), 7.22 (t, 2H, J=8.0 Hz), 7.31 (d, 1H, J=7.5 Hz), 7.41-7.60 (m, 5H), 7.80 (d, 1H, J=8.1 Hz), 7.97 (s, 1H), 8.16-8.21 (m, 1H), 8.39 (bd, 1H, J=7.4 Hz), 8.81 (d, 1H, J=6.8 Hz), 9.31 (s, 1H), 10.91 (s, 1H); ESIMS (M+H)+=661.

Sources & evidence

ORD record
ord-ee934b6538084862b57a8a722ad67386
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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