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

HRID 1159913Notes

Reaction equation

HRID 1159913 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.CC1C(C)=N[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([NH2:46])[CH:41]=2)N=1>>[CH2:2]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([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:41]=2)[CH2:5][CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 1460536-Quinoxalinamine, 2,3-dimethyl-HCID 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 2,3-dimethyl-6-quinoxalinamine by a procedure similar to Example 64. 1H NMR (400 MHz, DMSO-d6) δ 2.66 (s, 6H), 6.66 (d, 1H, J=5.4 Hz), 7.19 (t, 1H, J=6.9 Hz), 7.29 (t, 2H, J=8.0 Hz), 7.43 (d, 1H, J=7.7 Hz), 7.51-7.65 (m, 3H), 7.85-7.88 (m, 2H), 7.99-8.03 (dd, 1H, J=2.3, 9.0 Hz), 8.06 (s, 1H), 8.42 (d, 1H, J=5.3 Hz), 8.60-8.64 (m, 2H), 8.91 (d, 1H, J=6.9 Hz), 10.08 (s, 1H), 10.98 (s, 1H); ESIMS (M+H)+=558.

Sources & evidence

ORD record
ord-863b3ee8b0b44a39986ac6187fe10e9b
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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