Dimethylformamide → HCID 71113142, compound

HRID 716827Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-(trifluoromethyl)-1,3-dihydroisobenzofuran-5-ol (enantiomer 1) (Intermediate 28, 20 mg, 0.098 mmol) and 3-(6-fluoro-5-methyl-3-pyridyl)-5,5-dimethyl-imidazolidine-2,4-dione (Intermediate 6, 27.9 mg, 0.118 mmol) in DMF (1 mL) dipotassium carbonate (27.1 mg, 0.196 mmol) was added and the reaction mixture was stirred for 48 hours at 110° C. After cooling the mixture was diluted with water (5 ml) and extracted with ethyl acetate (2×10 ml). The organic layer was dried (Na2SO4), filtered and evaporated and the residue was purified by reverse phase flash chromatography on C18 column (MEGA BE Varian, 5 g) using water/acetonitrile from 100:0 to 0:100 as eluent affording the title compound (5 mg) as white solid.

Workup

temperatureAfter cooling the mixture
extractionextracted with ethyl acetate (2×10 ml)
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
customevaporated
customthe residue was purified by reverse phase flash chromatography on C18 column (MEGA BE Varian, 5 g)

Sources & evidence

ORD record: ord-fcfc17c84cdd4be3b70bb8863977e890
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193704B2

Reaction notes

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