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

HRID 1805383Notes

Reaction equation

HRID 1805383 reaction equation
Br[CH:2]=[CH:3]Br.[O:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][NH2:14])[CH2:7][CH2:6]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[C@:24]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][C:25]3=[O:33])[CH2:23]2)=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]2[C@@:24]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:2][CH2:3][NH:14][CH2:13][CH2:12][CH2:11][N:8]4[CH2:9][CH2:10][O:5][CH2:6][CH2:7]4)[C:25]3=[O:33])[CH2:23]2)=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 108971,2-DibromoetheneHCID 61055N-(3-Aminopropyl)morpholineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305419(1R,2S)-2-(4-chlorophenyl)-1'-(2-(3-morpholinopropylamino)ethyl) spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 81 starting from dibromo ethylene, 3-morpholinopropan-1-amine (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 C25H30ClN3O2: 439, observed (M+H)+: 440.1 1HNMR (400 MHz, MeOD-d4) δppm 2.07-2.32 (m, 6 H) 3.26 (s, 8 H) 3.47 (t, J=5.94 Hz, 3 H) 4.24 (d, J=28.55 Hz, 3 H) 6.12 (d, J=7.07 Hz, 1 H) 6.81 (t, J=7.07 Hz, 1 H) 7.14 (d, J=7.58 Hz, 1 H) 7.19-7.29 (m, 3H) 7.30-7.39 (m, 2 H).

Sources & evidence

ORD record
ord-c9d4d1205c7044df996fddfbb4391077
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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