Water → HCID 70981557, compound

HRID 1475389Notes

Reaction equation

HRID 1475389 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.[C:12]([O:16][C:17]([N:19]1[C:27]2[CH:26]=[C:25]([CH2:28]OS(C)(=O)=O)[N:24]=[CH:23][C:22]=2[C:21]([CH3:35])([CH3:34])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].O>C1COCC1>[C:12]([O:16][C:17]([N:19]1[C:27]2[CH:26]=[C:25]([CH2:28][N:7]3[CH:11]=[CH:10][CH:9]=[N:8]3)[N:24]=[CH:23][C:22]=2[C:21]([CH3:35])([CH3:34])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1048Pyrazole2×HCID 23665647Potassium tert-butoxide2×HCID 86724000HCID 86724000, compound

Product 1

HCID 70981557HCID 70981557, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of potassium tert-butoxide (0.090 g, 0.80 mmol) in anhydrous THF (4.0 mL) was added pyrazole (0.104 g, 1.52 mmol). The reaction was stirred for 30 min. 6-Methanesulfonyloxymethyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.271 g, 0.76 mmol) was added at ambient temperature and the reaction was stirred for 1 h. A second equivalent of pyrazole (104 mg) was added, followed by potassium tert-butoxide (90 mg) and the reaction stirred for 1 h. Water (4.0 mL) was added and the reaction extracted with EtOAc (3×5.0 mL), washed with saturated brine solution (15 mL), dried over sodium sulfate, filtered and concentrated. Chromatography (SiO2, gradient elution, 0-100%, EtOAc/petrol then SiO2, gradient elution, 0-5%, MeOH/DCM). gave the title compound (0.13 g, 52%) as a pale yellow oil MS: [M+H]+=329.

Workup

  1. stirringthe reaction was stirred for 1 h
  2. stirringthe reaction stirred for 1 h
  3. extractionthe reaction extracted with EtOAc (3×5.0 mL)
  4. washwashed with saturated brine solution (15 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washChromatography (SiO2, gradient elution, 0-100%, EtOAc/petrol
  9. washSiO2, gradient elution, 0-5%, MeOH/DCM)

Sources & evidence

ORD record
ord-690a2d99180b44db8bfd1ceafed95e03
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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