Hydrochloric Acid → 3-Ethyl 5-methYl 6-(difluoromethyl)-4-(cyanomethylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 255445Notes

Reaction equation

HRID 255445 reaction equation
[F:1][CH:2]([F:23])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5](Cl)[C:4]=1[C:19]([O:21][CH3:22])=[O:20].C(N(CC)CC)C.Cl.[NH2:32][CH2:33][C:34]#[N:35].Cl>CN(C=O)C>[F:1][CH:2]([F:23])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([NH:35][CH2:34][C:33]#[N:32])[C:4]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 140137713-Ethyl 5-methyl 6-(difluoromethyl)-4-chloro-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 140138573-Ethyl 5-methYl 6-(difluoromethyl)-4-(cyanomethylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.0 g (0.008 mol) of product of Example 103, 1.72 g (0.017 mol) of triethylamine and 0.79 g (0.008 mol) of aminoacetonitrile hydrochloride in 30 ml of DMF was stirred at 50° C. for 24 hours. The reaction mixture was cooled to room temperature and poured into 3.7% HCl. This solution was extracted with diethyl ether. The ether phase was washed with H2O, and dried (MgSO4) . The dry ether phase was concentrated in vacuo to 2.56 g of a brown semi-solid oil. The crude product was recrystallized in hexane/ethyl acetate to 0.9 g (28) of product as a beige solid; mp 87°-89° C.

Workup

  1. extractionThis solution was extracted with diethyl ether
  2. washThe ether phase was washed with H2O
  3. dry with materialdried (MgSO4)
  4. concentrationThe dry ether phase was concentrated in vacuo to 2.56 g of a brown semi-solid oil
  5. customThe crude product was recrystallized in hexane/ethyl acetate to 0.9 g (28) of product as a beige solid

Sources & evidence

ORD record
ord-7afa9374b5694675bb2aedd34fa4c95d
Source dataset
uspto-grants-1987_10
Patent number
US04698093

Reaction notes

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