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

HRID 1805318Notes

Reaction equation

HRID 1805318 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]2[C@:19]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH2:28][C:29]4[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=4)[C:32](O)=[O:33])[C:20]3=[O:38])[CH2:18]2)=[CH:13][CH:12]=1>>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[C@@:19]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH2:28][C:29]4[CH:37]=[CH:36][CH:35]=[C:31]([C:32]([N:7]5[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]5)=[O:33])[CH:30]=4)[C:20]3=[O:38])[CH2:18]2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 780131-IsopropylpiperazineHCID 53244689HCID 53244689, compound

Product 1

HCID 53244880(1R,2S)-2-(4-chlorophenyl)-1'-(3-(4-isopropylpiperazine-1-carbonyl)benzyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 60 starting from 1-isopropylpiperazine, (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 C31H32ClN3O2: 513, observed (M+H)+: 514.2 1H NMR (400 MHz, CDCl3) δppm 1.37 (d, J=6.32 Hz, 6 H) 2.04 (dd, J=7.71, 4.67 Hz, 1 H) 2.28 (dd, J=9.22, 4.67 Hz, 1 H) 2.86 (br. s., 2 H) 3.35 (t, J=8.46 Hz, 1 H) 3.61 (br. s., 6 H) 4.96 (d, J=15.92 Hz, 1H) 5.18 (d, J=16.17 Hz, 1 H) 6.02 (d, J=7.33 Hz, 1 H) 6.71-6.82 (m, 2 H) 7.06-7.19 (m, 3 H) 7.31 (s, 1 H) 7.33-7.39 (m, 1 H) 7.39-7.51 (m, 3 H).

Sources & evidence

ORD record
ord-d92a0e258abb447abe9254aea652642f
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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