Hydrochloric Acid → HCID 90449575, compound

HRID 1411299Notes

Reaction equation

HRID 1411299 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[CH:18][O:19]C)[CH:15]=3)[N:10]([C:21]([NH:23][C:24]3[S:25][C:26]([Cl:29])=[CH:27][N:28]=3)=[O:22])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].Cl.C(=O)([O-])O.[Na+].O>CC(C)=O>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH:18]=[O:19])[CH:15]=3)[N:10]([C:21]([NH:23][C:24]3[S:25][C:26]([Cl:29])=[CH:27][N:28]=3)=[O:22])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 131732216HCID 131732216, compound

Product 1

HCID 90449575HCID 90449575, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

1′-Acetyl-N-(5-chlorothiazol-2-yl)-5-(2-methoxyvinyl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (83 mg, 0.192 mmol) was dissolved in acetone (3 mL). Thereafter, 6 N hydrochloric acid (1.5 mL) was added to the above obtained solution, and the thus obtained mixture was then stirred at 50° C. for 2 hours. Thereafter, saturated sodium hydrogen carbonate and water were added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo, to obtain 1′-acetyl-N-(5-chlorothiazol-2-yl)-5-(2-oxoethyl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (66.1 mg, 82%) in the form of a yellow solid.

Workup

  1. extractionthe mixed solution was then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-680bd7613dd64103b310766488ba168b
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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