1-Methylpiperazine → HCID 58305341, compound

HRID 1805345Notes

Reaction equation

HRID 1805345 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CO[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13](I)[CH:12]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]2[C@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:37])[CH2:27]2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C@H:26]2[C@@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([C:13]4[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[O:18])[CH:12]=4)[C:29]3=[O:37])[CH2:27]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 531671-MethylpiperazineHCID 69258Methyl 3-iodobenzoateHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305341HCID 58305341, compound

Procedure

The title compound was prepared in analogy to Example 85 starting from 1-methylpiperazine, methyl-3-iodobenzoate (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 C28H26ClN3O2: 471, observed (M+H)+: 472.21H NMR (400 MHz, MeOD-d4) δppm 2.34 (dd, J=9.09, 5.05 Hz, 1 H) 2.43 (dd, J=8.59, 5.05 Hz, 1 H) 2.93 (s, 3 H) 3.17 (br. s., 4 H) 3.40 (t, J=8.84 Hz, 1 H) 3.62 (br. s., 4 H) 6.97 (d, J=7.83 Hz, 1 H) 7.16-7.25 (m, 2 H) 7.26-7.38 (m, 5 H) 7.49 (s, 1 H) 7.55 (t, J=7.71 Hz, 2 H) 7.67 (t, J=7.83 Hz, 1 H).

Sources & evidence

ORD record
ord-1d5de0a3b04a433fa2c1d7ffc7a6ee0c
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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