Hydrochloric Acid → N-(4,5,6,7-Tetrahydro-benzo[b]thiophen-2-yl)-2-(3-trifluoromethyl-4,5,6,7-tetrahydro indazol-1-yl)-acetamide

HRID 1162743Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([CH2:12][C:13]([NH:15][C:16]2[S:20][C:19]3[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=3[C:17]=2C(O)=O)=[O:14])[N:4]=1.Cl>N1C2C(=CC=CC=2)C=CC=1.O.[Cu]>[S:20]1[C:16]([NH:15][C:13](=[O:14])[CH2:12][N:5]2[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=3[C:3]([C:2]([F:29])([F:1])[F:28])=[N:4]2)=[CH:17][C:18]2[CH2:24][CH2:23][CH2:22][CH2:21][C:19]1=2

Participants

Conditions

Temperature: 200 °C

Procedure

2-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (200 mg, 0.47 mmol) and copper powder (45 mg, 0.70 mmol) were suspended in quinoline (4 mL) and the resulting mixture heated in a Biotage SmithCreator microwave at 200° C. for 10 min. The mixture was diluted with water (5 mL), acidified to pH 1 with 5 M HCl, and extracted with diethyl ether (3×50 mL). The combined organics were dried over sodium sulfate and concentrated in vacuo. The residue obtained was purified by silica gel chromatography using DCM as eluent, to afford the title compound as an off-white solid (170 mg, 0.44 mmol, 95%).

Workup

extractionextracted with diethyl ether (3×50 mL)
dry with materialThe combined organics were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue obtained
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-e74f268176d841f682598bc74df5406d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820707B2

Reaction notes

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