Methyl 3-(bromomethyl)benzoate → HCID 58305311, compound

HRID 1805372Notes

Reaction equation

HRID 1805372 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].CO[C:13](=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Br)[CH:15]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]2[C@:32]3([C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][C:33]3=[O:41])[CH2:31]2)=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C@@H:30]2[C@:32]3([C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]([CH2:20][C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([N:8]5[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]5)=[O:22])[CH:15]=4)[C:33]3=[O:41])[CH2:31]2)=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 7091611-(Methylsulfonyl)piperazineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305311HCID 58305311, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from 1-(methylsulfonyl)piperazine, 3-bromomethyl-benzoic acid methyl ester (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 C29H28ClN3O4S: 549, observed (M+H)+: 550.21H NMR (400 MHz, MeOD-d4) δppm 8.19-8.05 (m, 2 H) 7.49 (s, 3 H) 7.25 (br. s., 4 H) 7.09-7.05 (m, 1H) 6.88 (br. s., 2 H) 6.50 (br. s., 2 H) 5.29-5.12 (m, 2 H) 4.23 (d, J=7.58 Hz, 1 H) 3.64-3.56 (m, 1H) 3.41 (d, J=7.58 Hz, 1 H) 3.29-3.19 (m, 1 H) 3.11 (d, J=8.08 Hz, 2 H) 3.07-2.99 (m, 2 H) 2.98-2.91 (m, 2 H) 2.88-2.75 (m, 2 H).

Sources & evidence

ORD record
ord-aa5426c3fe0842e1bbdf16fc54a01712
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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