Piperazine → (1R,2S)-2-(4-chlorophenyl)-1'-(3-(piperazine-1-carbonyl)benzyl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805315Notes

Reaction equation

HRID 1805315 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@:16]3([C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([CH2:25][C:26]4[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=4)[C:29](O)=[O:30])[C:17]3=[O:35])[CH2:15]2)=[CH:10][CH:9]=1>>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[C@@:16]3([C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([CH2:25][C:26]4[CH:34]=[CH:33][CH:32]=[C:28]([C:29]([N:1]5[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]5)=[O:30])[CH:27]=4)[C:17]3=[O:35])[CH2:15]2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 53244689HCID 53244689, compound

Product 1

HCID 58305274(1R,2S)-2-(4-chlorophenyl)-1'-(3-(piperazine-1-carbonyl)benzyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 60 starting from piperazine, (3-bromomethyl)-benzoate (commercially available), (1R,2S) and (1S,2R)-3-((2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)methyl)benzoic acid prepared as in Scheme 1. LC/MS m/e calcd. for C28H26ClN3O2: 471, observed (M+H)+: 472.2 1H NMR (400 MHz, MeOD-d4) δppm 2.17-2.30 (m, 2 H) 3.51 (br. s., 8 H) 3.21-3.35 (m, 1 H) 5.04-5.23 (m, 2 H) 6.10 (d, J=7.58 Hz, 1 H) 6.74 (t, J=7.45 Hz, 1 H) 6.95 (d, J=7.83 Hz, 1 H) 7.05-7.16 (m, 1 H) 7.23 (d, J=8.34 Hz, 2 H) 7.29-7.38 (m, 2 H) 7.40-7.49 (m, 2 H) 7.49-7.58 (m, 2 H).

Sources & evidence

ORD record
ord-6f8e0e39485b435898fe23dac3c996f5
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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