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Methanol → 1-(4-Amino-2-methoxybenzenesulfonyl)-5-chloro-3-(cyclohexylmethyl)-1,3-dihydro-3-(methylamino)indol-2-one

HRID 234525
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HRID 234525 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=1[O:23][CH3:24])(=[O:13])=[O:12])[C:6](=[O:25])[C:5]2([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[NH:26][CH3:27].CO>[Ni].C1COCC1>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[C:5]([CH2:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)([NH:26][CH3:27])[C:6]2=[O:25])(=[O:12])=[O:13])=[C:15]([O:23][CH3:24])[CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 887MethanolHCID 190764665-Chloro-3-(cyclohexylmethyl)-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)-3-(methylamino)indol-2-one

생성물 1

HCID 190765121-(4-Amino-2-methoxybenzenesulfonyl)-5-chloro-3-(cyclohexylmethyl)-1,3-dihydro-3-(methylamino)indol-2-one수율 53.1%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 8028
Tetrahydrofuran
용매

실험 절차

A mixture of 1.2 g of the compound obtained in EXAMPLE 102, 3 g of Raney® nickel, 30 ml of MeOH and 40 ml of THF is hydrogenated at atmospheric pressure and at RT. After 40 minutes, the catalyst is filtered off on C elite® and the filtrate is evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (75/25; v/v) as the eluent to give 0.6 g of the expected product, which is used as such in the next step.

후처리

  1. customis hydrogenated at atmospheric pressure and at RT
  2. filtrationthe catalyst is filtered off on C elite®
  3. customthe filtrate is evaporated under vacuum
  4. customThe residue is chromatographed on silica

출처 및 근거

ORD 기록
ord-84db338b920048069d742aa6bf42d159
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05594023

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