5-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one → (S)-2-{3-[4-(5-Fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)piperidin-1-yl]-2-hydroxy-propoxy}-benzoic acid tert-butyl ester

HRID 132586Notes

Reaction equation

HRID 132586 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.[C:18]([O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH2:31][CH:32]1[CH2:34][O:33]1)([CH3:21])([CH3:20])[CH3:19]>C(O)(C)C>[C:18]([O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH2:31][C@@H:32]([OH:33])[CH2:34][N:13]1[CH2:12][CH2:11][CH:10]([N:6]2[C:5]3[CH:16]=[CH:17][C:2]([F:1])=[CH:3][C:4]=3[NH:8][C:7]2=[O:9])[CH2:15][CH2:14]1)([CH3:20])([CH3:19])[CH3:21]

Participants

4

Reactant 2

HCID 137921045-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 859153532-Oxiranylmethoxy-benzoic acid tert-butyl ester

Product 1

HCID 69199357(S)-2-{3-[4-(5-Fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)piperidin-1-yl]-2-hydroxy-propoxy}-benzoic acid tert-butyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5-fluoro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (235 mg, 0.5 mmol) and 2-oxiranylmethoxy-benzoic acid tert-butyl ester (250 mg, 1.0 mmol) in isopropanol (iPrOH) (10 mL) was stirred at 70° C. for 14 h, after which the solvent was removed in vacuo. The residue was purified by gradient flash chromatography on silica gel (CH2Cl2 to EtOH), yielding an off-white solid (240 mg, 99%).

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe residue was purified by gradient flash chromatography on silica gel (CH2Cl2 to EtOH)

Sources & evidence

ORD record
ord-0fa8bb63e4e24990a6e7aa75434177a8
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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