Water → HCID 178427183, compound

HRID 2054041Notes

Reaction equation

HRID 2054041 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[NH:6][C:7]([C@@H:9]([NH:20][C:21](=[O:36])[C:22]3[CH:27]=[CH:26][C:25]([C:28]([N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:29])=[C:24]([CH3:35])[CH:23]=3)[CH2:10][CH2:11][NH:12][S:13]([CH2:16][CH2:17][CH2:18]Cl)(=[O:15])=[O:14])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].O>CN(C)C=O>[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[NH:6][C:7]([C@@H:9]([NH:20][C:21](=[O:36])[C:22]3[CH:27]=[CH:26][C:25]([C:28]([N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:29])=[C:24]([CH3:35])[CH:23]=3)[CH2:10][CH2:11][N:12]3[CH2:18][CH2:17][CH2:16][S:13]3(=[O:14])=[O:15])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178427193HCID 178427193, compound

Product 1

HCID 178427183HCID 178427183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

130 mg (0.22 mmol) of N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(3-chloropropylsulfonylamino)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide is dissolved in 5 mL of dimethylformamide and, after the addition of 21 mg (0.45 mmol) of sodium hydride (50% in oil), stirred for 2 hours at ambient temperature. Then it is combined with water and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate and concentrated by evaporation. Yield: 90 mg (70%); Rf value: 0.40 (silica gel: dichloromethane/ethanol=9:1); C26H30ClN5O4S (544.077); mass spectrum: (M+H)+=545/547 (chlorine isotope).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts are dried over sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4361a53c7d11498290086bfd426c6b26
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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