1-(Thiazol-2-yl)piperazine → 5-chloro-3-(2-methoxyphenyl)-3-{2-oxo-2-[4-(1,3-thiazol-2-yl)piperazin-1-yl]ethyl}-1,3-dihydro-2H-indol-2-one

HRID 1662630Notes

Reaction equation

HRID 1662630 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH2:20][C:21](O)=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].[S:24]1[CH:28]=[CH:27][N:26]=[C:25]1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[CH2:20][C:21](=[O:22])[N:32]1[CH2:33][CH2:34][N:29]([C:25]2[S:24][CH:28]=[CH:27][N:26]=2)[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 9118061-(Thiazol-2-yl)piperazineHCID 21925457HCID 21925457, compound

Product 1

HCID 674300515-chloro-3-(2-methoxyphenyl)-3-{2-oxo-2-[4-(1,3-thiazol-2-yl)piperazin-1-yl]ethyl}-1,3-dihydro-2H-indol-2-oneYield 83.8%

Procedure

With 800 mg of [5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetic acid, which is the compound described in Preparation 1.1 of the brochure Publication No. WO03/008407, and 449 mg of 1-(1,3-thiazol-2-yl)piperazine as starting materials, reaction manipulation and post-treatment were carried out by a similar method to Step 45-1, and the obtained residue was crystallized from EtOAc and n-hexane to obtain 976 mg of the title compound (colorless crystal).

Workup

  1. customdescribed in Preparation 1.1 of the brochure Publication No
  2. custommaterials, reaction manipulation
  3. customthe obtained residue was crystallized from EtOAc and n-hexane

Sources & evidence

ORD record
ord-46a8850b980d423ea6cb203c3db53c68
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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