4-Toluenesulfonyl chloride → HCID 70976328, compound

HRID 455269Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:21][N:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH2:8][C@@H:4]2[CH2:3]1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.CCN(CC)CC>C(Cl)Cl>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][C@@H:2]2[CH2:21][N:5]3[C:6](=[O:20])[N:7]([C:9]4[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:17])[F:18])=[CH:11][CH:10]=4)[CH2:8][C@@H:4]3[CH2:3]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of (6S,7aS)-6-Amino-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 20, step d) (80 mg, 0.266 mmol), 4-Methyl-benzenesulfonyl chloride (101 mg, 0.53 mmol) and NEt3 (100 mg, 0.99 mmol) in DCM (10 mL) was stirred at 10° C. overnight. The mixture was washed with water (5 mL×3), dried with anhydrous sodium sulfate and then purified with silica gel column chromatography (eluting with DCM/MeOH=150:1) to 58 mg (46%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.72 (d, 2H, J=9 Hz), 7.31 (d, 2H, J=9 Hz), 7.24 (d, 2H, J=6 Hz), 7.04 (d, 2H, J=9 Hz), 6.00 (d, 1H, J=9 Hz), 4.07-4.00 (m, 1H) 3.76-3.74 (m, 2H), 3.49-3.36 (m, 2H), 3.22-3.19 (m, 1H), 2.47 (s, 3H), 2.23-2.15 (m, 1H), 1.55-1.44 (m, 1H); LC-MS: 456.1 [M+1]+.

Workup

washThe mixture was washed with water (5 mL×3)
dry with materialdried with anhydrous sodium sulfate
custompurified with silica gel column chromatography (eluting with DCM/MeOH=150:1) to 58 mg (46%) of the title compound as a white solid

Sources & evidence

ORD record: ord-0bf0ebda702d472388a6adec79c9c317
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497288B2

Reaction notes

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