Dimethylformamide → HCID 178504721, compound

HRID 2369061Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([CH2:28][C:29]#[N:30])=[N:9]1.[N-:31]=[N+:32]=[N-:33].[Na+].[NH4+].[Cl-].CN(C=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([CH2:28][C:29]2[NH:33][N:32]=[N:31][N:30]=2)=[N:9]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]acetonitrile (136 mg, 0.3 mmol), NaN3 (59 mg, 0.9 mmol), NH4Cl (49 mg, 0.9 mmol), and anhydrous DMF (5 mL) was stirred in a sealed vial at 120° C. for 24 h. The mixture was poured into water, and extracted with DCM. The combined extracts were washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-80% 20% MeOH/DCM) to give the title compound as a white solid (116 mg, 78%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.85-7.83 (m, 1H), 7.74-7.71 (m, 1H), 7.62-7.46 (m, 5H), 7.22 (d, 1H), 6.8 (d, 1H), 6.66 (s, 1H), 4.52 (s, 2H), 3.08 (s, 3H). MS(ES): 497 [M+H]+.

Workup

extractionextracted with DCM
washThe combined extracts were washed with water and brine
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe crude product was purified by flash chromatography (0-80% 20% MeOH/DCM)

Sources & evidence

ORD record: ord-385c29d8a1f841be855a41f790ea7c76
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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