Benzoyl chloride → HCID 57796667, compound

HRID 2099902Notes

Reaction equation

HRID 2099902 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]2[N:15]=[C:14]([N:16]3[CH2:20][CH:19]4[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH:18]4[CH2:17]3)[N:13]([CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])[C:12]=2[CH:36]=1.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C)C=O>[C:37]([NH:7][C:8]1[CH:9]=[CH:10][C:11]2[N:15]=[C:14]([N:16]3[CH2:17][CH:18]4[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[CH2:21][CH:19]4[CH2:20]3)[N:13]([CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])[C:12]=2[CH:36]=1)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 10796Cesium carbonateHCID 57796669HCID 57796669, compound

Product 1

HCID 57796667HCID 57796667, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14 mg (0.04 mmol) of cesium carbonate were added to a solution of 35 mg (0.09 mmol) of tert-butyl 5-[6-amino-1-(3-methylbut-2-enyl)-1H-benzimidazol-2-yl]hexahydropyrrolo[3,4-c]pyrrole-2-carboxylate in 5 ml of dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 10 μl (0.08 mmol) of benzoyl chloride were added and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure and purified by means of preparative HPLC (acetonitrile/water+0.5% trifluoroacetic acid, gradient: 20/80 to 100/0). 10 mg (22% of the desired compound were obtained.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by means of preparative HPLC (acetonitrile/water+0.5% trifluoroacetic acid, gradient: 20/80 to 100/0)

Sources & evidence

ORD record
ord-f2e63dd0086d418a880f105202723db5
Source dataset
uspto-grants-2009_08
Patent number
US07569700B2

Reaction notes

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