2-Pyrrolidone → HCID 53247647, compound

HRID 1805352Notes

Reaction equation

HRID 1805352 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].Br[C:8]1[CH:9]=[C:10]([CH:14]=[C:15](I)[CH:16]=1)[C:11]([OH:13])=[O:12].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]2[C@:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:36])[CH2:26]2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]2[C@@:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]([C:8]4[CH:9]=[C:10]([CH:14]=[C:15]([N:1]5[CH2:5][CH2:4][CH2:3][C:2]5=[O:6])[CH:16]=4)[C:11]([OH:13])=[O:12])[C:28]3=[O:36])[CH2:26]2)=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 120252-PyrrolidoneHCID 51825203-Bromo-5-iodobenzoic acidHCID 67232941(1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53247647HCID 53247647, compound

Procedure

The title compound was prepared in analogy to Example 92 starting from 2-pyrrolidone, 3-bromo-5-iodo-benzoic acid (commercially available), (1R,2R) and (1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C27H21ClN2O4: 472, observed (M+H)+: 4731.2 1HNMR (400 MHz, MeOD-d4) δppm 2.18-2.35 (m, 4 H) 2.67 (t, J=8.08 Hz, 2 H) 3.35-3.39 (m, 1 H) 4.05 (t, J=7.07 Hz, 2 H) 6.16 (d, J=7.07 Hz, 1 H) 6.82 (t, J=7.45 Hz, 1 H) 6.97 (d, J=7.33 Hz, 1 H) 7.12-7.20 (m, 1H) 7.34 (q, J=8.67 Hz, 4 H) 7.95 (s, 1 H) 8.20 (t, J=1.89 Hz, 1 H) 8.33 (s, 1 H).

Sources & evidence

ORD record
ord-000a6a59459948fbba023317787cf5d0
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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