Pyridine → HCID 20238652, compound

HRID 364960Notes

Reaction equation

HRID 364960 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14](O)([C:21]([F:24])([F:23])[F:22])[NH:13][C:12]([CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[C:11]3[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:7][CH:8]=[CH:9][C:2]=12.FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1>ClCCl>[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[NH:13][C:12]([CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[C:11]3[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 20238639HCID 20238639, compound

Product 1

HCID 20238652HCID 20238652, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diethyl 4-(4-benzofurazanyl)-2-diethoxymethyl-1,4,5,6-tetrahydro-6-hydroxy-6-(trifluoromethyl)-3,5-pyridinedicarboxylate (9.0 g, 17 mmoles), trifluoroacetic anhydride (4.77 ml, 34 mmoles) and pyridine (4.05 ml, 51 mmoles) in dry dichloromethane (100 ml) was stirred at room temperature. After 3 hours the solution was washed with water, 10% aqueous hydrochloric acid solution, brine and dried (MgSO4). Evaporation of the solvent left crude sub-title compound as an oil (8.8 g). Nmr (CDCl3) δ 6.1 (s,H), 5.6(s,H).

Workup

  1. washAfter 3 hours the solution was washed with water, 10% aqueous hydrochloric acid solution, brine
  2. dry with materialdried (MgSO4)
  3. customEvaporation of the solvent
  4. waitleft crude sub-title compound as an oil (8.8 g)

Sources & evidence

ORD record
ord-41b70cbfcefb4cbab9bd0c62d7050b90
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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