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

HRID 1366366Notes

Reaction equation

HRID 1366366 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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 1 N 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).

Workup

  1. washwashed with 1 N 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)

Sources & evidence

ORD record
ord-e7bbe1b4fcc542f595265cb63d692397
Source dataset
uspto-grants-2011_02
Patent number
US07893057B2

Reaction notes

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