Dimethylamine → 1-(3-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)-N,N-dimethylmethanamine

HRID 2193717Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of the chloride 148 (3.8 g, 8.42 mmol) in dimethylformamide (42 mL) was added dimethylamine (8.4 mL, 16.84 mmol) and the reaction mixture was heated to 60° C. After few hours the reaction was complete and the dimethylformamide was evaporated. The residue was triturated with ethyl acetate, collected by filtration, washed with ethyl acetate and dried to afford title compound 149 as a yellow solid (1.71 g, 48% yield). MS (m/z): 424.0 (M+H).

Workup

waitAfter few hours the reaction was complete
customthe dimethylformamide was evaporated
customThe residue was triturated with ethyl acetate
filtrationcollected by filtration
washwashed with ethyl acetate
customdried

Sources & evidence

ORD record: ord-bbbd51cfc13a48df95cce28f34e91c46
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329726B2

Reaction notes

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