Water → 3-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(1-pyrrolidylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 255415Notes

Reaction equation

HRID 255415 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]([Cl:15])([F:14])[F:13])[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)CC)C.Cl.[NH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.O>CN(C=O)C>[Cl:15][C:12]([F:13])([F:14])[C:6]1[N:5]=[C:4]([C:16]([F:17])([F:18])[F:19])[C:3]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:2]([NH:33][N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 140137593-Ethyl 5-methyl 4-chloro-6-(chlorodifluoromethyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 140137603-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(1-pyrrolidylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.0 g (0.013 mol) of product of Example 28, 3.42 g (0.034 mol) of triethylamine, 2.08 g (0.017 mol) of N-aminopyrrolidine hydrochloride in 30 ml of DMF were reacted at 45° C. for 1 hour. The reaction mixture was poured into water, extracted with ether, washed with diluted HCl, dried (MgSO4) and concentrated in vacuo to 4.06 g of light yellow solid. This solid was recrystallized in hot hexane affording 3.47 g (59.9%) of product as a beige solid; mp 101°-103° C.

Workup

  1. customwere reacted at 45° C. for 1 hour
  2. extractionextracted with ether
  3. washwashed with diluted HCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo to 4.06 g of light yellow solid
  6. customThis solid was recrystallized in hot hexane affording 3.47 g (59.9%) of product as a beige solid

Sources & evidence

ORD record
ord-10ead0b6bee340739c0b241eb4f11c41
Source dataset
uspto-grants-1987_10
Patent number
US04698093

Reaction notes

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