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 132592Notes

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

Participants

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

customThe volatiles were removed in vacuo and residue
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

Loading…