Thionyl Chloride → HCID 59603901, compound

HRID 1255871Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[N:11]([N:13]=[CH:14][C:15]=3[C:16]3[CH:17]=[C:18]([C:21]([NH:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[O:22])[S:19][CH:20]=3)[CH:12]=2)[CH:4]=[N:3]1.S(Cl)([Cl:31])=O>CN(C=O)C>[Cl:31][C:20]1[S:19][C:18]([C:21]([NH:23][CH2:24][C:25]([F:27])([F:28])[F:26])=[O:22])=[CH:17][C:16]=1[C:15]1[CH:14]=[N:13][N:11]2[CH:12]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:8]=[N:9][C:10]=12

Participants

Conditions

Temperature: 80 °C

Procedure

4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide (107 mg, 0.263 mmol) was taken up in thionyl chloride (2 ml, 27.4 mmol) and heated at 80° C. overnight. Evaporated solvent under vacuum and took up in 3 ml DMF, purified reverse-phase 30-100% ACN/H2O w/0.1% TFA. Evaporated solvent under vacuum to yield 60 mgs pale yellow solid (51.7%). LRMS [M+H]=441.0

Workup

custompurified reverse-phase 30-100% ACN/H2O

Sources & evidence

ORD record: ord-8638fdc834c742a69bad6539d9a819d7
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461162B2

Reaction notes

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