2-Bromo-1,1-dimethoxyethane → (1R,2S)-2-(4-chlorophenyl)-1'-(2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)ethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805328Notes

Reaction equation

HRID 1805328 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.CO[CH:14](OC)[CH2:15]Br.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]2[C@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:37])[CH2:27]2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C@H:26]2[C@@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([CH2:14][CH2:15][N:8]4[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][N:2]([CH3:11])[CH3:1])[CH2:6][CH2:7]4)[C:29]3=[O:37])[CH2:27]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305402(1R,2S)-2-(4-chlorophenyl)-1'-(2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)ethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 74 starting from 1-(2-Dimethylamino-ethyl)-piperazine, bromoacetaldehyde dimethyl acetal (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 C26H33ClN4O: 452, observed (M+H)+: 453.1 1HNMR (400 MHz, MeOD-d4) δppm 2.15-2.33 (m, 3 H) 2.86 (t, J=5.81 Hz, 3 H) 2.96 (s, 6 H) 3.27 (t, J=8.59 Hz, 3 H) 3.45-3.76 (m, 3 H) 4.32 (d, J=48.76 Hz, 3 H) 6.12 (d, J=7.58 Hz, 1 H) 6.81 (t, J=7.20 Hz, 1 H) 7.11-7.19 (m, 1 H) 7.20-7.28 (m, 3 H) 7.30-7.41 (m, 2 H).

Sources & evidence

ORD record
ord-19f6cd32f39c4a73a81869b900f71ec1
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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