Water → HCID 178503942, compound

HRID 1993628Notes

Reaction equation

HRID 1993628 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@:12]([NH:27][C:28]([NH:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[S:29])([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.I[CH3:40].O>CN(C=O)C>[C:31](/[N:30]=[C:28](\[S:29][CH3:40])/[NH:27][C@:12]([C:4]1[CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=[C:2]([F:1])[CH:3]=1)([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 58897182HCID 58897182, compound

Product 1

HCID 178503942HCID 178503942, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-N-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethylcarbamothioyl)benzamide (70 mg, 0.13 mmol), prepared by method described in Procedures 22, 23, 24 and 9, in DMF (0.5 mL), was added iodomethane (10 μL, 0.15 mmol). The reaction vessel was sealed and stirred at room temperature for 18 h, followed by the addition of H2O. The aqueous layer was extracted with EtOAc. The separated organic portion was dried over MgSO4, filtered and concentrated to give (S,Z)-methyl N′-benzoyl-N-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)carbamimidothioate as a white solid (58 mg, 81% yield). LCMS: RT=4.49 min [M+H] 554.92 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).

Workup

  1. customThe reaction vessel was sealed
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialThe separated organic portion was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f2a995b7cb746199ea2f99e3cb069de
Source dataset
uspto-grants-2010_01
Patent number
US07652023B2

Reaction notes

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