2-Thiopheneacetyl chloride → HCID 57737224, compound
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:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]([CH3:33])[CH3:32])[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:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[CH2:39][C:40](Cl)=[O:41]>>[CH3:32][N:31]([CH2:30][C:26]1[CH:25]=[C:24]([NH:23][C:19]2[N:18]=[C:17]([C:16]3[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:40](=[O:41])[CH2:39][C:35]5[S:34][CH:38]=[CH:37][CH:36]=5)[CH:7]=[CH:6][CH:5]=4)=[N:9][N:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=34)[CH:22]=[CH:21][N:20]=2)[CH:29]=[CH:28][CH:27]=1)[CH3:33]Participants
3
Procedure
The title compound was prepared from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-{3-[(dimethylamino)methyl]phenyl}-2-pyrimidinamine and 2-thiopheneacetyl chloride using acylation conditions described in Example 1, Step F to generate the product in 88% yield. 1H NMR (400 MHz, DMSO-d6): δ 2.11 (s, 6H), 3.26 (s, 2H), 3.86 (s, 2H), 6.46 (d, 1H, J=5.3 Hz), 6.85 (d, 1H, J=7.5 Hz), 6.96 (m, 2H), 7.10-7.19 (m, 2H), 7.26 (d, 1H, J=7.9 Hz), 7.36-7.48 (m, 3H), 7.62 (d, 1H, J=8.2 Hz), 7.69 (s, 1H), 7.73 (d, 1H, J=9.1 Hz), 7.89 (s, 1H), 8.23 (d, 1H, J=5.3 Hz), 8.51 (d, 1H, J=8.8 Hz), 8.82 (d, 1H, J=6.9 Hz), 9.52 (s, 1H), 10.35 (s, 1H); ES-LC/MS m/z=560 [M+H]+.
Sources & evidence
- ORD record
- ord-0679639e6bdc484eb9d0e731d92e9b49
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807673B2
Reaction notes
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