Hydrochloric Acid → HCID 14013858, compound

HRID 2291506Notes

Reaction equation

HRID 2291506 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].[CH2:24]([N:26](CC)[CH2:27]C)C.CNC.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]([N:26]([CH3:27])[CH3:24])[C:4]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 8471TriethylamineHCID 140137713-Ethyl 5-methyl 6-(difluoromethyl)-4-chloro-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 14013858HCID 14013858, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.46 g (0.010 mol) of the compound produced in Example 103, 0.97 g (0.010 mol) of triethylamine and 2.00 g (0.012 mol) of a 26% W/V solution of aqueous dimethylamine in 50 ml of DMF was stirred at room temperature for 18 hours. The reaction mixture was poured into 3.7% HCl and extracted with diethyl ether. The ether phase was washed with H2O, and dried (MgSO4). The dry ether phase was con-centrated in vacuo to 2.6 g of a yellow solid. This crude product was purified using the HPLC in 5% ethyl acetate/cyclohexane, affording 2.39 g (67%) of a yellow solid; mp 80°-81° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether phase was washed with H2O
  3. dry with materialdried (MgSO4)
  4. customThis crude product was purified

Sources & evidence

ORD record
ord-409ffcf0484844a0bca99e8f6e988fac
Source dataset
uspto-grants-1989_01
Patent number
US04797149

Reaction notes

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