Water → HCID 86596081, compound

HRID 1823786Notes

Reaction equation

HRID 1823786 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([O:17][S:18]([C:21]3[CH:26]=[CH:25][C:24](F)=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:39]1([NH2:44])[CH2:43][CH2:42][CH2:41][CH2:40]1.O>CN1CCCC1=O>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([O:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:44][CH:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2906CyclopentylamineHCID 86596080HCID 86596080, compound

Product 1

HCID 86596081HCID 86596081, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-fluoro-benzenesulfonic acid 3-benzyl-2-(3,4-dimethoxy-phenylamino)-3H-benzoimidazol-5-yl ester (151 mg) and cyclopentylamine (118 μl) in N-methylpyrrolidinone (1.5 ml) was heated at 110° C. in a sealed tube for 3 hours. The reaction mixture was allowed to cool then poured into water (30 ml) and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1, v/v) to give 4-cyclopentylamino-benzenesulfonic acid 3-benzyl-2-(3,4-dimethoxy-phenylamino)-3H-benzoimidazol-5-yl ester (122 mg) as a brown solid. Mass spectrum: 599 [M+H]+, retention time=4.0 minutes.

Workup

  1. temperatureto cool
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthen evaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1

Sources & evidence

ORD record
ord-f2792545ada84bf8bf3b69b525a5eeef
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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