5-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one → N-(5-Chloro-2-{3-[4-(5-fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)piperidin-1-yl]-2-hydroxy-propoxy}-phenyl)-acetamide

HRID 132588Notes

Reaction equation

HRID 132588 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:29][CH2:30][CH:31]2[CH2:33][O:32]2)=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[CH:24]=1>C(O)(C)C.CCO>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:29][CH2:30][CH:31]([OH:32])[CH2:33][N:13]2[CH2:12][CH2:11][CH:10]([N:6]3[C:5]4[CH:16]=[CH:17][C:2]([F:1])=[CH:3][C:4]=4[NH:8][C:7]3=[O:9])[CH2:15][CH2:14]2)=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[CH:24]=1

Participants

5

Reactant 2

HCID 137921045-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 22313737N-(5-chloro-2-oxiranylmethoxy-phenyl)-acetamide

Product 1

HCID 69198974N-(5-Chloro-2-{3-[4-(5-fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)piperidin-1-yl]-2-hydroxy-propoxy}-phenyl)-acetamideYield 100.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 5-fluoro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (480 mg, 2.0 mmol) and N-(5-chloro-2-oxiranylmethoxy-phenyl)-acetamide (490 mg, 2.0 mmol) in isopropanol (i-PrOH) (10 mL) and EtOH (10 mL) were stirred at 80° C. for 17 h, after which the solvent was removed in vacuo. The residue was purified using gradient flash chromatography (CH2Cl2 to MeOH), yielding the desired product as a white solid (960 mg, 99%).

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe residue was purified

Sources & evidence

ORD record
ord-f9faa3e395c1486e8a00d5b966711431
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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