2,5-Dimethoxytetrahydrofuran → HCID 22668852, compound

HRID 395403Notes

Reaction equation

HRID 395403 reaction equation
[NH2:1][C:2]1[C:3]([CH:19]2[CH2:22][CH2:21][CH2:20]2)=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]([CH:12]([F:14])[F:13])=[N:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CO[CH:25]1[CH2:29][CH2:28][CH:27](OC)O1>C(O)(=O)C.O>[F:13][CH:12]([F:14])[C:5]1[C:4]([C:15]([O:17][CH3:18])=[O:16])=[C:3]([CH:19]2[CH2:22][CH2:21][CH2:20]2)[C:2]([N:1]2[CH:25]=[CH:29][CH:28]=[CH:27]2)=[C:7]([C:8]([F:10])([F:11])[F:9])[N:6]=1

Participants

5

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 15117831HCID 15117831, compound

Product 1

HCID 22668852HCID 22668852, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1.62 g (5 mmol) of methyl 5-amino-2-(difluoromethyl) -4-cyclobutyl-6- (trifluoromethyl)-3-pyridinecarboxylate (example A-2 of U.S. Pat. No. 5,114,465) and 0.8 g (6 mmol) of 2,5-dimethoxy-tetrahydrofuran in 10 ml of acetic acid as heated at 70° C. for 2.5 h. The reaction mixture was then diluted with 100 ml of water and extracted with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate (3×100 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (10% EtOAc in hexane) to give the product, mp 70-71° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with saturated sodium bicarbonate (3×100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (10% EtOAc in hexane)
  6. customto give the product, mp 70-71° C.

Sources & evidence

ORD record
ord-0949102fa62049b881e573c9377cf77a
Source dataset
uspto-grants-2003_08
Patent number
US06605624B1

Reaction notes

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