Water → HCID 178522508, compound

HRID 1823792Notes

Reaction equation

HRID 1823792 reaction equation
C(O[C:6]([NH:8][C:9]1[NH:10][C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1)=[O:7])(C)(C)C.[OH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[OH2:36]>CN1CCCC1=O>[OH:29][CH:30]1[CH2:35][CH2:34][N:33]([C:6]([NH:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([O:18][S:19]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[N:33]4[CH2:34][CH2:35][CH:30]([OH:36])[CH2:31][CH2:32]4)(=[O:21])=[O:20])=[CH:17][C:11]=3[N:10]=2)=[O:7])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 962WaterHCID 79341Piperidin-4-olHCID 86596073HCID 86596073, compound

Product 1

HCID 178522508HCID 178522508, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-fluoro-benzenesulfonic acid 2-tert-butoxycarbonylamino-3H-benzoimidazol-5-yl ester (200 mg, example 55 (Step 3) and 4-hydroxypiperidine (554 mg) in N-methylpyrrolidinone (6 ml) was heated at 110° C. for 24 hours. The reaction mixture was then poured into water (120 ml) and extracted three times with ethyl acetate (50 ml). The combined extracts were dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95 C: 5, v/v) to give (4-hydroxy-piperidin-1-yl)-benzenesulfonic acid 2-[(4-hydroxy-piperidine-1-carbonyl)-amino]-1H-benzoimidazol-5-yl ester (125 mg) as a beige solid. Mass Spectrum: 516 [M+H]+, retention time=6.51 minutes.

Workup

  1. extractionextracted three times with ethyl acetate (50 ml)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95 C

Sources & evidence

ORD record
ord-288c82b05307438281aec3ca546a3ae6
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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