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

HRID 1805317Notes

Reaction equation

HRID 1805317 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]2[C@:22]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:31][C:32]4[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=4)[C:35](O)=[O:36])[C:23]3=[O:41])[CH2:21]2)=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]2[C@:22]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:31][C:32]4[CH:40]=[CH:39][CH:38]=[C:34]([C:35]([N:10]5[CH2:9][CH2:8][N:7]([C:4]6[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=6)[CH2:12][CH2:11]5)=[O:36])[CH:33]=4)[C:23]3=[O:41])[CH2:21]2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 53244689HCID 53244689, compound

Product 1

HCID 58305401(1S,2R)-2-(4-chlorophenyl)-1'-(3-(4-(pyridin-4-yl)piperazine-1-carbonyl)benzyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 60 starting from 1-(pyridin-4-yl)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 C33H29ClN4O2: 548, observed (M+H)+: 549.1 1H NMR (400 MHz, MeOD-d4) δppm 2.20-2.29 (m, 2 H) 3.26-3.31 (m, 1 H) 3.58 (br. s., 4 H) 3.88 (br. s., 4 H) 5.08-5.25 (m, 2 H) 6.14 (d, J=7.58 Hz, 1 H) 6.77 (t, J=7.58 Hz, 1 H) 6.92 (d, J=7.83 Hz, 1 H) 7.12 (t, J=7.20 Hz, 3 H) 7.21-7.32 (m, 4 H) 7.41 (s, 1 H) 7.45 (d, J=7.33 Hz, 1 H) 7.50-7.61 (m, 2 H) 8.19 (d, J=7.58 Hz, 2 H).

Sources & evidence

ORD record
ord-67b0a9b26b59476fbdf66ce685397023
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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