Hydrochloric Acid → HCID 89736045, compound

HRID 1748660Notes

Reaction equation

HRID 1748660 reaction equation
[C:1]([C:3]1([C:13]2[N:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[CH:23]=[N:24][N:25]([C:27]4[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=4)[CH:26]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1)#[N:2].O.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[C:1]([C:3]1([C:13]2[N:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[CH:23]=[N:24][N:25]([C:27]4[CH:28]=[CH:29][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:32]=4)[CH:26]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6](=[O:7])[CH2:5][CH2:4]1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 89734858HCID 89734858, compound

Product 1

HCID 89736045HCID 89736045, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-1-(4-isopropylphenyl)-1H-pyrazole-4-carboxamide (236 mg) in a mixture of acetic acid (5 ml), water (1 ml) and 1N hydrochloric acid aqueous solution (1 ml) was stirred at 100° C. for two hours. After completion of the reaction, a saturated aqueous solution of potassium carbonate was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography to give the titled compound (216 mg).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified with column chromatography

Sources & evidence

ORD record
ord-3e23dd4c9fa2482ea30e7bcaae22aa26
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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