Potassium tert-butoxide → N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(2-oxoimidazolidin-1-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2053898Notes

Reaction equation

HRID 2053898 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]2[NH:6][C:7]([C@@H:9]([NH:19][C:20](=[O:35])[C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[O:28])=[C:23]([CH3:34])[CH:22]=3)[CH2:10][CH2:11][NH:12][C:13]([NH:15][CH2:16][CH2:17]Cl)=[O:14])=[N:8][C:4]=2[CH:3]=1.CC(C)([O-])C.[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]2[NH:6][C:7]([C@@H:9]([NH:19][C:20](=[O:35])[C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)=[O:28])=[C:23]([CH3:34])[CH:22]=3)[CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][NH:15][C:13]3=[O:14])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178427187HCID 178427187, compound

Product 1

HCID 178427184N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(2-oxoimidazolidin-1-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

0.1 g (0.257 mmol) of N-{(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-[3-(2-chloroethyl)ureido]propyl}-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide is dissolved in 5 mL of dimethylformamide and, after the addition of 50 mg (0.45 mmol) of potassium tert-butoxide, stirred for 5 hours at 40° C. Then the mixture is poured onto ice water and extracted with dichloromethane. The combined organic extracts are dried over sodium sulfate and concentrated by evaporation. The crude product is triturated with diethyl ether and suction filtered. Yield: 61%; Rf value: 0.70 (silica gel; dichloromethane/ethanol=4:1); C26H29ClN6O3 (509.01); mass spectrum: (M+H)+=509/511 (chlorine isotope) and (M−H)−=507/509 (chlorine isotope).

Workup

  1. additionThen the mixture is poured onto ice water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic extracts are dried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe crude product is triturated with diethyl ether and suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e13f2a107f07466eab70cde369179e21
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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