Acryloyl chloride → HCID 178460021, compound

HRID 64316Notes

Reaction equation

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

Participants

Reactant 2

HCID 13140Acryloyl chloride

HCID 178513495HCID 178513495, compound

Product 1

HCID 178460021HCID 178460021, compound

Procedure

The desired product was prepared from 2-(3-aminophenyl)-6-(4-phenoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carboxamide and acryloyl chloride using the procedure similar to that for compound 8. 1H NMR (400 MHz, CD3OD-d4) δ 8.06 (s, 1H), 7.83 (s, 1H), 7.64 (d, J=8.4 Hz, 1H), 7.52-7.38 (m, 5H), 7.15 (t, J=7.6 Hz, 1H), 7.09-7.05 (m, 4H), 6.49-6.37 (m, 2H) and 5.80 (dd, J=4.0, 8.8 Hz, 1H). MS (ESI) m/e [M+1]+ 463.9.

Sources & evidence

ORD record: ord-8fff9330f119409fb0c237ea121a32fa
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447106B2

Reaction notes

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