Methyl 3-iodobenzoate → HCID 53245850, compound

HRID 1805343Notes

Reaction equation

HRID 1805343 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].CO[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16](I)[CH:15]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C@H:29]2[C@:31]3([C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[NH:33][C:32]3=[O:40])[CH2:30]2)=[CH:25][CH:24]=1>>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C@@H:29]2[C@@:31]3([C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]([C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([N:8]5[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]5)=[O:21])[CH:15]=4)[C:32]3=[O:40])[CH2:30]2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 69258Methyl 3-iodobenzoateHCID 7091611-(Methylsulfonyl)piperazineHCID 67232941(1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53245850HCID 53245850, compound

Procedure

The title compound was prepared in analogy to Example 85 starting from 1-methanesulfonyl-piperazine, methyl-3-iodobenzoate (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 C28H26ClN3O4S: 535, observed (M+H)+: 536.2 1H NMR (400 MHz, MeOD-d4) δppm 2.22-2.36 (m, 2 H) 2.90 (s, 3 H) 3.35-3.39 (m, 1 H) 3.58-4.01 (m, 8 H) 6.16 (d, J=7.58 Hz, 1 H) 6.82 (t, J=7.58 Hz, 1 H) 6.95 (d, J=7.58 Hz, 1 H) 7.16 (t, J=7.83 Hz, 1H) 7.27-7.40 (m, 4 H) 7.58 (d, J=7.33 Hz, 1 H) 7.62-7.79 (m, 3 H).

Sources & evidence

ORD record
ord-926ca705f1244ae6a0648ee80f66191e
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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