Methanesulfonamide → (1S,2R)-3-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)-N-(methylsulfonyl)benzamide

HRID 1805377Notes

Reaction equation

HRID 1805377 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.[CH3:13][S:14]([NH2:17])(=[O:16])=[O:15].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[C:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:36])[CH2:26]2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]2[C@:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]([CH2:10][C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[C:3]([NH:17][S:14]([CH3:13])(=[O:16])=[O:15])=[O:12])[C:28]3=[O:36])[CH2:26]2)=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 72879MethanesulfonamideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 672320902-(4-Chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53244367(1S,2R)-3-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)-N-(methylsulfonyl)benzamide

Procedure

The title compound was prepared in analogy to Example 60 starting from 3-bromomethyl-benzoic acid methyl ester, methylsulfonamide (commercially available), (1R,2S) and 1S, 2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C25H21ClN2O4S: 480, observed (M+H)+: 481.2 1HNMR (400 MHz, DMSO-d6) δppm 2.08-2.18 (m, 1 H) 2.35-2.42 (m, 1 H) 2.92 (s, 3 H) 3.13-3.25 (m, 2 H) 4.95-5.13 (m, 2 H) 6.15 (d, 1 H) 6.70 (t, 1 H) 6.87 (d, 1 H) 7.02-7.10 (m, 2 H) 7.30-7.44 (m, 6H) 7.81-7.89 (m, 2 H).

Sources & evidence

ORD record
ord-6c867569970e49e1aec451cb46fd5a71
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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