Benzoyl chloride → HCID 69057323, compound

HRID 2099900Notes

Reaction equation

HRID 2099900 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][CH2:19][CH:18]4[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH:17]34)[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[CH2:20][CH2:19][CH:18]4[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[CH2:23][CH:17]34)[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 57796670HCID 57796670, compound

Product 1

HCID 69057323HCID 69057323, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17 mg (0.05 mmol) of cesium carbonate were added to a solution of 43 mg (0.1 mmol) of tert butyl 1-[6-amino-1-(3-methylbut-2-enyl)-1H-benzimidazol-2-yl]hexahydropyrrolo-[3,4-b]pyrrole-5-carboxylate in 5 ml of dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 12 μl (0.10 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 (20%) 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-e279bc5bf31043b1b1120f1c4119b8d2
Source dataset
uspto-grants-2009_08
Patent number
US07569700B2

Reaction notes

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