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

HRID 1649664Notes

Reaction equation

HRID 1649664 reaction equation
[F:1][CH:2]([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15]C)=[O:14])=[C:5](OC(C)C)[C:4]=1[C:21]([O:23][CH3:24])=[O:22].C(N([CH2:31][CH3:32])CC)C.[ClH:33].[NH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.O>CN(C=O)C>[Cl:33][C:2]([F:1])([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]([C:13]([O:15][CH2:31][CH3:32])=[O:14])=[C:5]([NH:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[C:4]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 14013781HCID 14013781, compound

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 23, 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-b892eb22bec54bc996fb27f06dbba739
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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