Cesium carbonate → HCID 86656923, compound

HRID 411009Notes

Reaction equation

HRID 411009 reaction equation
Cl.Cl.[NH:3]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([NH:18][C:19]4[S:20][C:21]5[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:22]=5[N:23]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:4]1.Br[CH2:33][CH2:34][OH:35].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:35][CH2:34][CH2:33][N:3]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([NH:18][C:19]4[S:20][C:21]5[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:22]=5[N:23]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:4]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 86656924HCID 86656924, compound

Product 1

HCID 86656923HCID 86656923, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-(6-Chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid [(S)-1-(2-hydroxy-ethyl)-pyrrolidin-3-yl]amide (20 mg) was prepared starting from 2-(6-chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid (S)-pyrrolidin-3-ylamide dihydrochloride (200 mg), 2-bromo-ethanol (50 uL) and Cs2CO3 (300 mg) in DMF (1 mL). The reaction was heated to 50° C. for 8 h. The reaction was filtered and purified with silica gel chromatography using DCM10% methanol in DCM (100:0 to 0:100) as an eluent system to give pure product. LC/MS: m/z 470.8.

Workup

  1. filtrationThe reaction was filtered
  2. custompurified with silica gel chromatography
  3. customto give pure product

Sources & evidence

ORD record
ord-18736fefe0974cb9ad412e423eb92689
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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