2-chloro-N,N-dimethylacetamide → HCID 58875132, compound

HRID 2355253Notes

Reaction equation

HRID 2355253 reaction equation
C(=O)([O-])O.[K+].[C:6]1([S:12]([NH:15][C:16]2[CH:17]=[C:18]([C@@H:22]([OH:42])[CH2:23][NH:24][C:25]([CH3:41])([CH3:40])[CH2:26][CH2:27][N:28]3[C:36]4[C:31](=[CH:32][C:33]([C:37]([OH:39])=[O:38])=[CH:34][CH:35]=4)[CH:30]=[CH:29]3)[CH:19]=[CH:20][CH:21]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[CH2:44][C:45]([N:47]([CH3:49])[CH3:48])=[O:46]>CN(C=O)C.O>[C:6]1([S:12]([NH:15][C:16]2[CH:17]=[C:18]([C@@H:22]([OH:42])[CH2:23][NH:24][C:25]([CH3:40])([CH3:41])[CH2:26][CH2:27][N:28]3[C:36]4[C:31](=[CH:32][C:33]([C:37]([O:39][CH2:44][C:45](=[O:46])[N:47]([CH3:49])[CH3:48])=[O:38])=[CH:34][CH:35]=4)[CH:30]=[CH:29]3)[CH:19]=[CH:20][CH:21]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 758862-chloro-N,N-dimethylacetamideHCID 516893Potassium BicarbonateHCID 16660493HCID 16660493, compound

Product 1

HCID 58875132HCID 58875132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium hydrogen carbonate (141 mg, 1.4 mmol) is added to a solution of 1-{3-[(R)-2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylic acid-hydrotrifluoroacetate (Example 6; 300 mg, 0.47 mmol) in 2 ml DMF. Then the reaction mixture is stirred for 20 minutes at RT and 2-chloro-N,N-dimethylacetamide (143 mg, 1.18 mmol) is added. After 90 hours stirring at RT the reaction mixture is diluted with 50 ml of water and extracted with ethyl acetate. The organic phase is dried on magnesium sulphate and the solvent is eliminated in vacuo. The residue is chromatographed on silica gel (DCM/methanol=100:0→95:5).

Workup

  1. stirringAfter 90 hours stirring at RT the reaction mixture
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is dried on magnesium sulphate
  4. customThe residue is chromatographed on silica gel (DCM/methanol=100:0→95:5)

Sources & evidence

ORD record
ord-2b53f318cdbb4bbfb20b8e1b182317ea
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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