Potassium Hydroxide → HCID 86621560, compound

HRID 1712969Notes

Reaction equation

HRID 1712969 reaction equation
CC1[N:3]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH2:18][CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[OH:25])[N:16]([C:26]([C:28]4[S:32][C:31]([C:33]5[CH:47]=[CH:46][CH:45]=[CH:44][C:34]=5[CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:30][CH:29]=4)=[O:27])[N:15]=3)=[CH:10][CH:9]=2)C(C)=CC=1.Cl.NO.[OH-].[K+]>CCO.O>[NH2:3][C:8]1[N:13]=[CH:12][C:11]([C:14]2[CH2:18][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[OH:25])[N:16]([C:26]([C:28]3[S:32][C:31]([C:33]4[CH:47]=[CH:46][CH:45]=[CH:44][C:34]=4[CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[CH:30][CH:29]=3)=[O:27])[N:15]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86621561HCID 86621561, compound

Product 1

HCID 86621560HCID 86621560, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of tert-butyl [2-(5-{[3-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}-2-thienyl)benzyl]carbamate (0.09 g, 0.14 mmol) in EtOH (1.7 mL) and water (0.75 mL) in a round-bottomed flask equipped with a reflux condenser was added hydroxylamine hydrochloride (0.58 g, 8.3 mmol) and potassium hydroxide (0.31 g, 5.6 mmol). The mixture was heated to 110° C. and allowed to stir vigorously for 5 h. The reaction was then cooled to rt and diluted with water. The aqueous solution was extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give tert-butyl [2-(5-{[3-(6-aminopyridin-3-yl)-5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}-2-thienyl)benzyl]carbamate as a white solid (0.04 g, 48%). LCMS: (FA) ES+ 570.6 (M+1).

Workup

  1. temperatureThe reaction was then cooled to rt
  2. extractionThe aqueous solution was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-53db289ab1ee4d048853ddea454f6719
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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