Acryloyl chloride → 7-(2-Acrylamidophenyl)-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 64276Notes

Reaction equation

HRID 64276 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[N:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)[C:16]([C:17]([NH2:19])=[O:18])=[C:12]2[NH:11][CH2:10][CH2:9]1.[C:34](Cl)(=[O:37])[CH:35]=[CH2:36]>>[C:34]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[N:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)=[CH:22][CH:21]=3)[C:16]([C:17]([NH2:19])=[O:18])=[C:12]2[NH:11][CH2:10][CH2:9]1)(=[O:37])[CH:35]=[CH2:36]

Participants

3

Reactant 2

HCID 13140Acryloyl chlorideHCID 1369280927-(2-Aminophenyl)-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 1369837097-(2-Acrylamidophenyl)-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

Procedure

The desired product was prepared from 7-(2-aminophenyl)-2-(4-(4-fluorophenoxyl)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carboxamide and acryloyl chloride using the procedure similar to that for compound 8. 1H NMR (400 MHz, CD3OD-d4) δ 7.47 (d, J=8.4 Hz, 2H), 7.39 (t, J=7.6 Hz, 1H), 7.33 (t, J=7.6 Hz, 1H), 7.26 (t, J=7.6 Hz, 1H), 7.12-7.00 (m, 6H), 6.81 (d, J=8.0 Hz, 1H), 6.53-6.46 (m, 1H), 6.39-6.35 (m, 1H), 5.87-5.76 (m, 1H), 5.73-5.69 (m, 1 H), 3.36-3.30 (m, 1H), 3.22-3.17 (m, 1H), 2.45-2.39 (m, 1 H) and 2.17-2.14 (m, 1H). MS (ESI) m/e [M+1]+ 497.9.

Sources & evidence

ORD record
ord-d0f761da83aa4dcba010cbe200c0af83
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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