2-chloro-N,N-dimethylacetamide → HCID 59632867, compound

HRID 2369100Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([C:16]3[N:20]([C:21]4[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=4)[N:19]=[C:18]([C:28]([F:31])([F:30])[F:29])[CH:17]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C[O-].[Na+].Cl[CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38]>CO>[CH3:40][N:39]([CH3:41])[C:37](=[O:38])[CH2:36][O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([N:20]2[C:16]([C:14]3[S:15][C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=4)=[CH:12][CH:13]=3)=[CH:17][C:18]([C:28]([F:31])([F:29])[F:30])=[N:19]2)[CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-(5-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenol (120 mg, 0.26 mmol) was dissolved in anhydrous methanol (10.0 mL). To this solution was added a 25 wt % solution of NaOMe in methanol (130 μL, 0.57 mmol) and 2-chloro-N,N-dimethyl-acetamide (156 mg, 128 mmol). The reaction mixture was heated to reflux at 80° C. under nitrogen atmosphere for overnight. It was cooled off and concentrated in vacuo. The residue was purified by column chromatography (50% ethyl acetate in hexane) to yield the product (87 mg, 61% yield). 1H-NMR (Acetone-d6): δ 8.21 (m, 1H), 8.03 (m, 1H), 7.96 (m, 1H), 7.76 (m, 1H), 7.65 (m, 1H), 7.52 (m, 1H), 7.25-7.16 (br, 5H), 4.94 (s, 2H), 3.25 (s, 3H), 3.09 (s, 3H), 2.90 (s, 3H), 2.88 (s, 3H). MS (ES): 550 [M+H]+

Workup

temperatureThe reaction mixture was heated
temperatureIt was cooled off
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-6b2c01c1c9444620820a06a0c92ec3ca
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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