Sodium hydride → HCID 68748332, compound

HRID 1254954Notes

Reaction equation

HRID 1254954 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH:15]2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:20])(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[CH3:10].Cl[CH2:29][N:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[N:31]1>CN(C=O)C>[N:30]1([CH2:29][N:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH:15]2[CH2:16][CH2:17][CH2:18][N:14]2[S:11]([C:6]2[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]([Cl:3])[CH:5]=2)(=[O:13])=[O:12])=[O:20])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[N:31]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 33282221-(Chloromethyl)-1H-benzotriazoleHCID 68749177HCID 68749177, compound

Product 1

HCID 68748332HCID 68748332, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Under inert atmosphere, to a stirred solution of NaH (12 mg, 0.31 mmol) in 0.20 ml anhydrous DMF at 0° C., was added a solution of parent compound 1-((3-chloro-4-methylphenyl)sulfonyl)-N-phenylpyrrolidine-2-carboxamide (0.040 g, 0.11 mmol) in 0.60 ml anhydrous DMF. After 1 h at 0° C., a solution of 1-(chloromethyl)-1H-benzotriazole (0.052 g, 0.31 mmol) in 0.50 ml anhydrous DMF was added to the reaction mixture. This mixture was stirred for 16 h, and then solvent was completely removed. The crude was chromatographically purified over SiO2 using Hexane/AcOEt as the eluant, yielding 0.024 g (46%) of the desired product.

Workup

  1. customsolvent was completely removed
  2. customThe crude was chromatographically purified over SiO2

Sources & evidence

ORD record
ord-e795b6697fed4bdc95f92a926ff9b7f5
Source dataset
uspto-grants-2013_06
Patent number
US08455660B2

Reaction notes

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