Sodium hydride → HCID 16059601, compound

HRID 1716427Notes

Reaction equation

HRID 1716427 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[N:31]1([C:37](Cl)=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[C:37]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:38])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2420851-Piperidinecarbonyl chlorideHCID 16059348HCID 16059348, compound

Product 1

HCID 16059601HCID 16059601, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 30 mg of 1-[1-(6-chloro-1H-indole-3-carbonyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one in 1 ml of DMF were added 1.1 eq. of NaH (55% in oil). The reaction mixture was stirred for 30 min. before the addition of 1.2 eq. of piperidine-1-carbonyl chloride. The crude reaction mixture was purified by preparative HPLC to afforded 21 mg of the title compound as a yellow powder.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-e7d2276705124c18984980a38810dd7a
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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