Acetic Acid → HCID 25056269, compound

HRID 1660770Notes

Reaction equation

HRID 1660770 reaction equation
[NH2:1][C@H:2]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C@H:7]1[CH2:13][O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:5].[C:29]([OH:32])(=[O:31])[CH3:30]>C(OCC)(=O)C>[C:29]([OH:32])(=[O:31])[CH3:30].[NH2:1][C@H:2]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C@H:7]1[CH2:13][O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:5]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 25022354Evogliptin

Product 1

HCID 25056269HCID 25056269, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

500 mg of the compound obtained in Example 11 was dissolved in 3 mL of ethyl acetate to which a solution of 74.5 mg of acetic acid in 1 mL of ethyl acetate was then slowly added followed by stirring for 30 min. The reaction mixture was concentrated, to which 2 mL of ethyl acetate and 1 mL of 2-propanol were then added followed by stirring. 15 mL of hexane was added thereto, and the resulting mixture was stirred for 10 min and filtered to afford 495 mg of the title compound as a solid.

Workup

  1. additionwas then slowly added
  2. concentrationThe reaction mixture was concentrated, to which 2 mL of ethyl acetate and 1 mL of 2-propanol
  3. additionwere then added
  4. stirringby stirring
  5. addition15 mL of hexane was added
  6. stirringthe resulting mixture was stirred for 10 min
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5613cbe92bf14c96bef291073117611f
Source dataset
uspto-grants-2011_10
Patent number
US08030315B2

Reaction notes

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