Dimethylformamide → N-(3-Fluoro-4-methanesulfonylamino-benzyl)-3-[2-(3-hydroxy-pyrrolidin-1-yl)-6-trifluoromethyl-pyridin-3-yl]-acrylamide

HRID 2265976Notes

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[C:16]([F:25])[CH:15]=2)=[O:11])=[CH:6][CH:5]=[C:4]([C:26]([F:29])([F:28])[F:27])[N:3]=1.CN(C=O)C.[NH:35]1[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36]1>CCOC(C)=O>[F:25][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:13][NH:12][C:10](=[O:11])[CH:9]=[CH:8][C:7]1[C:2]([N:35]2[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36]2)=[N:3][C:4]([C:26]([F:29])([F:28])[F:27])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide (40 mg, 0.088 mmol) in pyrrolidin-3-ol (0.4 ml) was added DMF (0.5 ml). The mixture was stirred for 12 hours at 110° C. The reaction mixture was diluted with EtOAc and then washed two times with 1N-HCl and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was column-chromatographed to yield the title compound (40 mg, 91%).

Workup

washwashed two times with 1N-HCl and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was column-chromatographed

Sources & evidence

ORD record: ord-46ffbd004caf4923a287146f52ca8ba5
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858621B2

Reaction notes

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