Hydrochloric Acid → HCID 90308963, compound

HRID 2283708Notes

Reaction equation

HRID 2283708 reaction equation
C1(P([N:15]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH:18]1([N:22]2[CH:30]=[C:29]3[C:24]([CH:25]=[CH:26][C:27](C(O)=O)=[CH:28]3)=[N:23]2)[CH2:21][CH2:20][CH2:19]1.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(N(CC)CC)C>[CH:18]1([N:22]2[CH:30]=[C:29]3[C:24]([CH:25]=[CH:26][C:27]([NH2:15])=[CH:28]3)=[N:23]2)[CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 199401P,P-Diphenylphosphinic azideHCID 90308824HCID 90308824, compound

Product 1

HCID 90308963HCID 90308963, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

Diphenylphosphoryl azide (4.15 mL) and triethylamine (3.76 mL) were added to a solution of 2-cyclobutyl-2H-indazole-5-carboxylic acid obtained in the above-described Step 1 (3.26 g) in 1,4-dioxane (50 mL), and the reaction solution was stirred at room temperature for 2 hours and 20 minutes. Thereafter, 1 N hydrochloric acid (100 mL) was added to the reaction solution, and then the reaction solution was stirred at 100° C. for 30 minutes. The reaction solution was cooled to room temperature, and potassium carbonate (14 g) was slowly added. The reaction solution was extracted with ethyl acetate, and then the organic layer was washed with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 2-cyclobutyl-2H-indazol-5-amine as a light yellow solid.

Workup

  1. stirringthe reaction solution was stirred at 100° C. for 30 minutes
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washthe organic layer was washed with a saturated saline solution
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under vacuum
  7. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-03c53d8990e94ac589f8b8173953414f
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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