Ethanol → 2-{3-(4-Hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetic acid

HRID 1821458노트

반응식

HRID 1821458 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([O:16]CC)=[O:15])[N:11]=[C:10]3[C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([NH:27][C:28]([NH:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[O:29])[C:24]=4[C:25](=[O:26])[C:9]=23)=[CH:4][CH:3]=1.O1CCOCC1.C(O)C.[OH-].[Na+]>CCOC(C)=O.CS(C)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([OH:16])=[O:15])[N:11]=[C:10]3[C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([NH:27][C:28]([NH:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[O:29])[C:24]=4[C:25](=[O:26])[C:9]=23)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 136352541Ethyl 2-{3-(4-hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetate

생성물 1

HCID 1357740212-{3-(4-Hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetic acid

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

Compound 37 (1.2 g, 2.4 mmol) was dissolved in 60 ml 3:2:1; dioxane:ethanol:DMSO and 12 ml 0.5 N NaOH added and the reaction became red. The reaction mixture was stirred at room temperature for one hour, diluted with EtOAc and washed with 1N HCl. The aqueous layer was back extracted once with ethyl acetate and the combined organic layers dried over MgSO4 and concentrated to an orange solid. The solid was triturated with 10 ml MeOH/100 ml Et2O, filtered off and dried to a solid (1.1 g, 2.4 mmol, 100%, compound 38: designated G7).

후처리

  1. washwashed with 1N HCl
  2. extractionThe aqueous layer was back extracted once with ethyl acetate
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated to an orange solid
  5. customThe solid was triturated with 10 ml MeOH/100 ml Et2O
  6. filtrationfiltered off
  7. dry with materialdried to a solid (1.1 g, 2.4 mmol, 100%, compound 38: designated G7)

출처 및 근거

ORD 기록
ord-322009dc97ac4b4284db031d2380b603
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605175B2

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