1,2-Dibromoethene → (1R,2S)-2-(4-chlorophenyl)-1'-(2-(2-(2,6-dimethylmorpholino) ethylamino) ethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805386Notes

Reaction equation

HRID 1805386 reaction equation
[CH3:1][CH:2]1[CH2:7][N:6]([CH2:8][CH2:9][NH2:10])[CH2:5][CH:4]([CH3:11])[O:3]1.Br[CH:13]=[CH:14]Br.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]2[C@:25]3([C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][C:26]3=[O:34])[CH2:24]2)=[CH:19][CH:18]=1>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C@H:23]2[C@@:25]3([C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]([CH2:13][CH2:14][NH:10][CH2:9][CH2:8][N:6]4[CH2:7][CH:2]([CH3:1])[O:3][CH:4]([CH3:11])[CH2:5]4)[C:26]3=[O:34])[CH2:24]2)=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 108971,2-DibromoetheneHCID 27564232-(2,6-Dimethylmorpholin-4-yl)ethanamineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53244509(1R,2S)-2-(4-chlorophenyl)-1'-(2-(2-(2,6-dimethylmorpholino) ethylamino) ethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 81 starting from 2-(2,6-dimethylmorpholino)ethanamine, dibromo ethylene (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 C26H32ClN3O2: 453, observed (M+H)+: 454.1 1HNMR (400 MHz, MeOD-d4) δppm 1.22 (dd, J=6.32, 2.27 Hz, 2 H) 1.26-1.37 (m, 6 H) 2.15-2.32 (m, 3 H) 2.43-2.67 (m, 1 H) 2.88 (br. s., 3 H) 3.26 (d, J=8.59 Hz, 2 H) 3.40-3.62 (m, 4 H) 3.70-3.96 (m, 1 H) 4.13 (br. s., 4 H) 6.05-6.21 (m, 1 H) 6.81 (t, J=7.58 Hz, 1 H) 7.06-7.18 (m, 1 H) 7.24 (d, J=8.34 Hz, 3 H) 7.29-7.38 (m, 2 H).

Sources & evidence

ORD record
ord-dfe9f4ebcbc448f192d277caf324a647
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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