(1-methyl-1H-imidazol-5-yl)methanol → 1'-({6-Chloro-1-[(1-methyl-1H-imidazol-5-yl)methyl]-1H-indol-3-yl}carbonyl)-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

HRID 1865990Notes

Reaction equation

HRID 1865990 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=5[C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:29][N:30]1[C:34]([CH2:35]OS(C)(=O)=O)=[CH:33][N:32]=[CH:31]1.CN1C(CO)=CN=C1>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=5[C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[CH2:35][C:34]2[N:30]([CH3:29])[CH:31]=[N:32][CH:33]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 2773450(1-methyl-1H-imidazol-5-yl)methanolHCID 596576231'-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-oneHCID 86610241methanesulfonic acid 3-methyl-3H-imidazol-4-ylmethyl ester

Product 1

HCID 596575201'-({6-Chloro-1-[(1-methyl-1H-imidazol-5-yl)methyl]-1H-indol-3-yl}carbonyl)-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Procedure

Following the general procedure III as described above, the alkylation of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (prepared according to example 19) with methanesulfonic acid 3-methyl-3H-imidazol-4-ylmethyl ester (prepared by mesylation of the commercially available (3-methyl-3H-imidazol-4-yl)-methanol) gave the title compound. ES-MS m/e (%): 493.1 (M+H+).

Sources & evidence

ORD record
ord-b865e7dd5f8049ae8cd000a1213249c2
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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