Dimethylformamide → HCID 87304235, compound

HRID 547797Notes

Reaction equation

HRID 547797 reaction equation
CN(C)C(N(C)C)=S.IC.[F:11][C:12]([F:52])([F:51])[C:13]1[CH:14]=[C:15]([C:23]([CH3:50])([CH3:49])[C:24]([N:26]([C:28]2[CH:29]=[N:30][C:31]([N:42]3[CH2:46][CH2:45][CH2:44][C@H:43]3[CH2:47][OH:48])=[CH:32][C:33]=2[C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=2[CH3:41])[CH3:27])=[O:25])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.[H-].[Na+].[CH3:55][N:56]([CH3:59])[CH:57]=[O:58]>CCCCCC.O>[F:52][C:12]([F:11])([F:51])[C:13]1[CH:14]=[C:15]([C:23]([CH3:49])([CH3:50])[C:24]([N:26]([CH3:27])[C:28]2[C:33]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[CH3:41])=[CH:32][C:31]([N:42]3[CH2:46][CH2:45][CH2:44][C@H:43]3[CH2:47][O:48][C:57](=[O:58])[N:56]([CH3:59])[CH3:55])=[N:30][CH:29]=2)=[O:25])[CH:16]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:18]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 177251,1,3,3-Tetramethyl-2-thioureaHCID 24758Sodium hydrideHCID 71457524HCID 71457524, compound

Product 1

HCID 87304235HCID 87304235, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a solution of 44 mg (0.33 mmol) 1,1,3,3-tetramethyl-2-thiourea in 1.5 ml N,N-dimethylformamide were added 0.027 ml iodomethane at room temperature. After stirring for 50 min. 0.20 g (0.33 mmol) (S)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-methyl-phenyl)-6-(2-hydroxymethyl-pyrrolidin-1-yl)-pyridin-3-yl]-N-methyl-isobutyramide and a suspension of 45 mg (0.90 mmol) sodium hydride (ca. 50% dispersion in mineral oil) in 0.5 ml n-hexane were added. After stirring at room temperature for 1 h the reaction mixture was diluted with water and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulphate and concentrated. Flash column chromatography gave 90 mg (40%) of the title compound as an off-white solid.

Workup

  1. additionwere added
  2. stirringAfter stirring at room temperature for 1 h the reaction mixture
  3. extractionextracted with three portions of tert-butyl methyl ether
  4. dry with materialThe combined organic extracts were dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-04a5145247c84d138186e3acab229139
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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