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5-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one → 5-Fluoro-1-(1-{(2S)-2-hydroxy-3-[(2-methyl-1H-indol-7-yl)oxy]propyl}4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 132592
Notes
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Reaction equation

HRID 132592 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.[CH3:18][C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][C:22]=2[O:28][CH2:29][C@@H:30]1[CH2:32][O:31]1>C(O)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:32][C@H:30]([OH:31])[CH2:29][O:28][C:22]4[CH:23]=[CH:24][CH:25]=[C:26]5[C:21]=4[NH:20][C:19]([CH3:18])=[CH:27]5)[CH2:14][CH2:15]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 137921045-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 865928342-methyl-7-[(2S)-oxiranylmethoxy]-1H-indole

Product 1

HCID 691988225-Fluoro-1-(1-{(2S)-2-hydroxy-3-[(2-methyl-1H-indol-7-yl)oxy]propyl}4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 70.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one (13.7 mg, 0.058 mmol), 2-methyl-7-[(2S)-oxiranylmethoxy]-1H-indole (12 mg, 0.058 mmol) in ethanol (2 mL) was kept on stirring at 80° C. for 5 h. The volatiles were removed in vacuo and residue purified by silica gel flash chromatography to give titled compound (18 mg).

Workup

  1. customThe volatiles were removed in vacuo and residue
  2. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-62327d64a690409bb3918058bfc76fb2
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07388020B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes