2-Thiopheneacetyl chloride → N-[3-(3-{2-[(2-Methyl-1,2,3,4-tetrahydro-7-isoquinolinyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:33]=[C:32]5[C:27]([CH2:28][CH2:29][N:30]([CH3:34])[CH2:31]5)=[CH:26][CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[S:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[CH2:40][C:41](Cl)=[O:42]>>[CH3:34][N:30]1[CH2:29][CH2:28][C:27]2[C:32](=[CH:33][C:24]([NH:23][C:19]3[N:18]=[C:17]([C:16]4[C:8]([C:4]5[CH:3]=[C:2]([NH:1][C:41](=[O:42])[CH2:40][C:36]6[S:35][CH:39]=[CH:38][CH:37]=6)[CH:7]=[CH:6][CH:5]=5)=[N:9][N:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=45)[CH:22]=[CH:21][N:20]=3)=[CH:25][CH:26]=2)[CH2:31]1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from N-{4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-2-methyl-1,2,3,4-tetrahydro-7-isoquinolinamine and 2-thiopheneacetyl chloride using acylation conditions described in Example 1, Step F to generate the product in 89% yield. 1H NMR (400 MHz, DMSO-d6): δ 2.31 (s, 3H), 2.57 (t, 2H, J=5.7 Hz), 2.74 (t, 2H, J=5.6 Hz), 3.38 (s, 2H), 3.88 (s, 2H), 6.47 (d, 1H, J=5.3 Hz), 6.97 (m, 3H), 7.13 (t, 1H, J=6.8 Hz), 7.27 (d, 1H, J=7.5 Hz), 7.38-7.50 (m, 5H), 7.75 (d, 1H, J=8.1 Hz), 7.90 (s, 1H), 8.23 (d, 1H, J=5.3 Hz), 8.46 (d, 1H, J=8.6 Hz), 8.83 (d, 1H, J=7.0 Hz), 9.43 (s, 1H), 10.36 (s, 1H). ES-LC/MS m/z=572 [M+H]+.
Sources & evidence
- ORD record
- ord-79a85f01b28d4aa58b9d4cc34e5b78a0
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807673B2
Reaction notes
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