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

HRID 1805378Notes

Reaction equation

HRID 1805378 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].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H: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>>[F: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 67233318HCID 67233318, compound

Product 1

HCID 67234413(1S,2R)-3-((2-(4-fluorophenyl)-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-fluorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C25H21FN2O4S: 470, observed (M+H)+: 471.2 1HNMR (400 MHz, DMSO-d6) δppm 2.10-2.18 (m, 1 H) 2.33-2.42 (m, 1 H) 3.18-3.27 (m, 1 H) 3.38 (s, 3 H) 5.10 (s, 2 H) 6.12 (d, 1 H) 6.71 (t, 1 H) 6.89-6.97 (m, 1 H) 7.03-7.09 (m, 1 H) 7.11-7.18 (m, 2H) 7.31-7.41 (m, 2 H) 7.48-7.55 (m, 1 H) 7.56-7.63 (m, 1 H) 7.82-7.93 (m, 2 H).

Sources & evidence

ORD record
ord-1a1297f6c5af4c3a9b1b333b314e9223
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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