Formic Acid → HCID 86728492, compound

HRID 2277779Notes

Reaction equation

HRID 2277779 reaction equation
C(N(CC)CC)C.C(O)=O.[CH2:11]([O:13][C:14](=[O:32])[CH:15]([CH2:19][C:20]1[C:25](Cl)=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[C:21]=1[F:31])[C:16](=[O:18])[CH3:17])[CH3:12]>CC(O)C.O.[Pd]>[CH2:11]([O:13][C:14](=[O:32])[CH:15]([CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[C:21]=1[F:31])[C:16](=[O:18])[CH3:17])[CH3:12]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 90302024HCID 90302024, compound

Product 1

HCID 86728492HCID 86728492, compound

Reagents, catalysts & solvents 2

HCID 23219155Palladium hydrateCatalystHCID 3776IsopropanolSolvent

Procedure

After cooling the reaction mixture to room temperature, a solution of triethylamine (670 μL, 4.9 mmol) and formic acid (150 μL, 4.0 mmol) in 2-propanol (1.1 mL) and 20% Pd(OH)2 carbon (19 mg; water content: 50%) were added, and after warming to 50° C., the mixture was stirred for 4.5 hours. The reaction mixture was subjected to HPLC analysis under the same conditions as HPLC conditions (2) of Example 10, and the purities of the title compound and its precursor (2-[(2-acetylamino-5-chloro-3-fluoropyridin-4-yl)methyl]-3-oxobutanoic acid ethyl ester) were calculated from their respective area ratios.

Workup

  1. temperatureafter warming to 50° C.

Sources & evidence

ORD record
ord-e51e98eb4be140a79551ce268d37956d
Source dataset
uspto-grants-2015_09
Patent number
US09133174B2

Reaction notes

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