Chloroacetone → HCID 59161249, compound

HRID 545531Notes

Reaction equation

HRID 545531 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[F:6][C:7]1[CH:8]=[C:9]([CH:33]=[CH:34][CH:35]=1)[CH2:10][N:11]1[C:23]2[CH2:22][CH2:21][C@@H:20]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[C:15]([C:30](=[S:32])[NH2:31])[CH:16]=2>CN(C=O)C.O>[F:6][C:7]1[CH:8]=[C:9]([CH:33]=[CH:34][CH:35]=1)[CH2:10][N:11]1[C:23]2[CH2:22][CH2:21][C@@H:20]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[CH2:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[C:15]([C:30]1[S:32][CH:2]=[C:3]([CH3:4])[N:31]=1)[CH:16]=2

Participants

5

Reactant 2

HCID 6571ChloroacetoneHCID 59161227HCID 59161227, compound

Product 1

HCID 59161249HCID 59161249, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combine chloroacetone (0.197 g, 2.13 mmol) and (R)-N-(9-(3-fluorobenzyl)-6-thiocarbamoyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Preparation 22) (0.300 g, 0.708 mmol) and heat at 80° C. in DMF under nitrogen for 2.5 h. Upon cooling, dilute the mixture with water and collect the precipitate by filtration. Slurry the precipitate in hot EtOAc to give 0.278 g of a yellow solid. MS (ES): m/z 462 (M+1); HPLC: Rt=3.33 min (100%).

Workup

  1. temperatureUpon cooling
  2. customcollect the precipitate
  3. filtrationby filtration

Sources & evidence

ORD record
ord-225fd404a3c44ba0a4009b8ba424d288
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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