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

HRID 2055505Notes

Reaction equation

HRID 2055505 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.[CH:29]1([C:32]2[O:36][C:35]([CH3:37])=[N:34][C:33]=2[CH2:38]OS(C)(=O)=O)[CH2:31][CH2:30]1>>[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[CH2:38][C:33]2[N:34]=[C:35]([CH3:37])[O:36][C:32]=2[CH:29]2[CH2:31][CH2:30]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 596576231'-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-oneHCID 86610240Methanesulfonic acid 5-cyclopropyl-2-methyl-oxazol-4-ylmethyl ester

Product 1

HCID 596576961'-({6-Chloro-1-[(5-cyclopropyl-2-methyl-1,3-oxazol-4-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 5-cyclopropyl-2-methyl-oxazol-4-ylmethyl ester (prepared by mesylation of (5-cyclopropyl-2-methyl-oxazol-4-yl)-methanol) gave the title compound. ES-MS m/e (%): 534.2(M+H+).

Sources & evidence

ORD record
ord-315ee5853c534253bde7cebecec8465a
Source dataset
uspto-grants-2008_02
Patent number
US07332501B2

Reaction notes

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