Ethyl Acetate → HCID 67465600, compound

HRID 1907141Notes

Reaction equation

HRID 1907141 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][NH:13][N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2].[H-].[Na+].FC(F)(F)S(O[CH2:42][C:43]([F:46])([F:45])[F:44])(=O)=O.CCOC(C)=O>C1COCC1.O>[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][N:13]([CH2:42][C:43]([F:46])([F:45])[F:44])[N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178492656HCID 178492656, compound

Product 1

HCID 67465600HCID 67465600, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-{[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carbonyl]-amino}-5-methyl-2H-indazole-7-carboxylic acid isopropylamide (500 mg, 1.07 mmol) and NaH (60%) (67 mg, 1.6 mmol) in THF (5 mL) was stirred for 1 hour at ambient temperature, and was treated with 2,2,2-trifluoroethyl trifluoromethanesulfonate (246 mg, 1.06 mmol). The resulting reaction mixture was stirred for 4 hours at 60° C. AcOEt and water was added. The phases were separated. The aqueous layer was extracted with AcOEt. The organic layers were washed with water, combined, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash-chromatography (SiO2, Toluene/AcOEt 7:3) afforded the title compound as a colorless crystalline solid. M.p. 178-181° C., LC/MS: 550 (M+H)+, 572/574 (M+Na)+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 4 hours at 60° C
  3. customThe phases were separated
  4. extractionThe aqueous layer was extracted with AcOEt
  5. washThe organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash-chromatography (SiO2, Toluene/AcOEt 7:3)

Sources & evidence

ORD record
ord-55752f7d5c38475790832794425c6bbc
Source dataset
uspto-grants-2013_12
Patent number
US08598078B2

Reaction notes

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