Dimethylamine → (S)-N-(5-(3-((dimethylamino)methyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 473079Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-N-(5-(3-(chloromethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.090 mmol, 40 mg) in DMF (1 mL) was added dimethylamine (2M solution, 0.224 mmol, 0.112 mL). The whole was heated to 60° C. for 2 h before the reaction mixture was purified directly by prep HPLC to give the title compound. (21.2 mg, 52%). MS (ESI): m/z [M+H]+ 455.2

Workup

customwas purified directly by prep HPLC

Sources & evidence

ORD record: ord-16ac077c009a4da2ae1a7615db351b6c
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633237B2

Reaction notes

Loading…