Acetic Acid → Ethyl 4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917757

Reaction equation

HRID 917757 reaction equation
Cl[C:2]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:32])([F:31])[C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])=[CH:16][C:15]=2[F:33])[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.COS([O:39][CH3:40])(=O)=O.[CH2:41](N(CC)CC)C.C[C:49](O)=[O:50]>C(Cl)(Cl)Cl.CCO>[F:33][C:15]1[CH:16]=[C:17]([C:20]([F:31])([F:32])[C:21]([F:30])([F:29])[C:22]([F:27])([F:28])[C:23]([F:25])([F:26])[F:24])[CH:18]=[CH:19][C:14]=1[NH:13][C:11]1[C:5]([C:6]([O:39][CH2:40][CH3:41])=[O:7])=[CH:4][N:3]([CH3:2])[C:49](=[O:50])[CH:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 23631003Ethyl 6-chloro-4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]nicotinate

Product 1

HCID 23630709Ethyl 4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylateYield 47%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

Ethyl 6-chloro-4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]nicotinate was dissolved in CHCl3 and reacted with Me2SO4, followed by triethylamine, AcOH and EtOH as described for example 33, step B. Purification by recrystallisation (EtOAc/Hexane) gave ethyl 4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (47%). 1H NMR [400 MHz, (CD3)2SO] δ 9.50 (s, 1H), 8.35 (s, 1H), 7.58 (t, J=8.3 Hz, 1H), 7.52 (dd, J=10.9, 1.8 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 5.59 (s, 1H), 4.08 (q, J=7.1 Hz, 2H), 3.22 (s, 3H), 1.10 (t, J=7.1 Hz, 3H).

Workup

  1. customPurification
  2. customby recrystallisation (EtOAc/Hexane)

Sources & evidence

ORD record
ord-cc0f1b67f1cf4c988de8659705a8d0d1
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Linked notes

Loading…