1,2-Dibromoethene → (1R,2S)-2-(4-chlorophenyl)-1'-(2-(2-morpholinoethylamino)ethyl) spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805384Notes

Reaction equation

HRID 1805384 reaction equation
Br[CH:2]=[CH:3]Br.[O:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][NH2:13])[CH2:7][CH2:6]1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[C@:23]3([C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[CH2:22]2)=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C@H:21]2[C@@:23]3([C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:2][CH2:3][NH:13][CH2:12][CH2:11][N:8]4[CH2:9][CH2:10][O:5][CH2:6][CH2:7]4)[C:24]3=[O:32])[CH2:22]2)=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 108971,2-DibromoetheneHCID 4082852-MorpholinoethylamineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53244447(1R,2S)-2-(4-chlorophenyl)-1'-(2-(2-morpholinoethylamino)ethyl) spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 81 starting from dibromo ethylene, 2-morpholinoethanamine (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 C24H28ClN3O2: 425, observed (M+H)+: 426.2 1HNMR (400 MHz, MeOD-d4) δppm 2.09-2.34 (m, 3 H) 3.02 (br. s., 4 H) 3.17 (t, J=6.19 Hz, 2 H) 3.27 (t, J=8.72 Hz, 1 H) 3.44-3.61 (m, 4 H) 3.87 (t, J=4.67 Hz, 4 H) 4.12-4.45 (m, 2 H) 6.11 (d, J=7.83 Hz, 1 H) 6.80 (t, J=7.58 Hz, 1 H) 7.10-7.18 (m, 1 H) 7.20-7.27 (m, 3 H) 7.29-7.40 (m, 2 H).

Sources & evidence

ORD record
ord-e543b41840f540d6bf0392d8c4fbc7cf
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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