Hydrochloric Acid → HCID 86729420, compound

HRID 521245Notes

Reaction equation

HRID 521245 reaction equation
Cl.[NH2:2][C:3]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]([C:11]2([CH2:21][C:22]#[N:23])[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]2)[N:4]=1.C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[NH2:2][C:3]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]([C:11]2([CH2:21][C:22]#[N:23])[CH2:20][CH2:19][C:14](=[O:15])[CH2:13][CH2:12]2)[N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86729421HCID 86729421, compound2×

Product 1

HCID 86729420HCID 86729420, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Aqueous hydrochloric acid (1 N, 36 mL, 36 mmol) was added to a solution of 3-amino-1-(8-(cyanomethyl)-1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrazole-4-carboxamide (Intermediate 35-5) (5.5 g, 18 mmol) in THF (106 mL). The reaction vessel was capped with a reflux condenser and heated to 80° C. for 2 hours. The reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate, and neutralized with saturated aqueous sodium bicarbonate solution. The organic layer was separated and then washed with brine. The washed solution was dried over sodium sulfate, the dried solution was filtered, and the filtrate was concentrated to afford the title compound, which was used without further purification.

Workup

  1. customThe reaction vessel was capped with a reflux condenser
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialThe washed solution was dried over sodium sulfate
  6. filtrationthe dried solution was filtered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ddac5ebfba124d16a93a972d4469e975
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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