Tert-Butylamine → 3-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(t-butylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 255422Notes

Reaction equation

HRID 255422 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:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[Cl:15][C:12]([F:13])([F:14])[C:6]1[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[C:3]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:2]([NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 140137593-Ethyl 5-methyl 4-chloro-6-(chlorodifluoromethyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 140138093-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(t-butylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylateYield 19.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared as described in Example 37: 5.0 g (0.013 mol) of product of Example 28, 3.9 ml (0.036 mol) of t-butylamine in 30 ml of DMF were reacted affording a residue which was kugelrohr distilled at 133 Pa, pot temperature 126° C., giving 4.49 g. Purification by HPLC using 5% ethyl acetate/cyclohexane as eluting solvent afforded 1.12 g of product as a white solid; mp 51.5°-53° C.

Workup

  1. customThis compound was prepared
  2. customaffording a residue which
  3. distillationwas kugelrohr distilled at 133 Pa, pot temperature 126° C.
  4. customgiving 4.49 g
  5. customPurification by HPLC
  6. washas eluting solvent

Sources & evidence

ORD record
ord-3cf757056f344597b233506f41de2226
Source dataset
uspto-grants-1987_10
Patent number
US04698093

Reaction notes

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