Isopropylamine → (1S,2R)-3-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)-N-isopropylbenzamide

HRID 1805314Notes

Reaction equation

HRID 1805314 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[C@:14]3([C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27]([OH:29])=O)[C:15]3=[O:33])[CH2:13]2)=[CH:8][CH:7]=1>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C@@H:12]2[C@:14]3([C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:29])[C:15]3=[O:33])[CH2:13]2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 53244689HCID 53244689, compound

Product 1

HCID 58305333(1S,2R)-3-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)-N-isopropylbenzamide

Procedure

The title compound was prepared in analogy to Example 60 starting from isopropyl amine, (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 C27H25ClN2O2: 444, observed (M+H)+: 445.2 1H NMR (400 MHz, MeOD-d4) δppm 1.23 (d, J=6.82 Hz, 6 H) 2.21 (d, J=8.59 Hz, 2 H) 3.21-3.28 (m, 1 H) 4.07-4.25 (m, 1 H) 5.10 (s, 2 H) 6.05 (d, J=7.58 Hz, 1 H) 6.69 (t, J=7.58 Hz, 1 H) 6.88 (d, J=7.83 Hz, 1 H) 7.05 (t, J=7.83 Hz, 1 H) 7.16-7.25 (m, 2 H) 7.25-7.34 (m, 2 H) 7.37-7.52 (m, 2 H) 7.69 (d, J=7.58 Hz, 1 H) 7.78 (s, 1 H).

Sources & evidence

ORD record
ord-8e39a7bfdd8a4158a45f3d4c19d5f175
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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