Hydrochloric Acid → HCID 71279111, compound

HRID 1621118Notes

Reaction equation

HRID 1621118 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[C:5]([C:24]([O:26]CC)=[O:25])[CH:4]=[N:3]1.[Li+].[OH-].Cl>C1COCC1.C(O)C>[CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[C:5]([C:24]([OH:26])=[O:25])[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71279164HCID 71279164, compound

Product 1

HCID 71279111HCID 71279111, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-methyl-5-(2-(5-methyl-2-phenyloxazol-4-yl)ethylcarbamoyl)-1H-pyrazole-4-carboxylate (407 mg, 1.06 mmol) in THF (3.00 mL) and Ethanol (1.5 mL) was added LiOH (1M aqueous solution, 2.13 mL, 2.13 mmol) at 0-5° C. The reaction mixture was stirred at RT for 2 h and poured into HCl (1 M, 2.15 mL). The resulting thick suspension was filtered and the filtrate was extracted with dichloromethane (3×50 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo to give 341 mg (90.4%) off-white solid as crude product which was used without any further purification.

Workup

  1. filtrationThe resulting thick suspension was filtered
  2. extractionthe filtrate was extracted with dichloromethane (3×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-666471902990410b9807411393db2145
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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