Methanol → HCID 67280524, compound

HRID 1958206Notes

Reaction equation

HRID 1958206 reaction equation
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[C:9]([C:11](=[O:32])[NH:12][C:13]2[CH:14]=[N:15][C:16]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH:18]=2)[CH:8]=[N:7][CH:6]=1)C.C1COCC1.CO>O>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[CH:18]=[C:13]([NH:12][C:11]([C:9]3[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=3)[C:4]([OH:33])=[O:3])=[O:32])[CH:14]=[N:15][C:16]=2[O:26][CH2:27][C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 67280736HCID 67280736, compound

Product 1

HCID 67280524HCID 67280524, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-[5-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylcarbamoyl]-nicotinic acid ethyl ester (510 mg, 1.06 mmol) was combined with THF (25 mL), methanol (5 mL) and water (5 mL) to give a light yellow suspension. The reaction mixture was stirred for 4 h, and concentrated in vacuo. The reaction mixture was poured into 100 mL ethyl acetate and extracted with 1 M HCl (1×25 mL) and brine (1×25 mL). The aqueous layer phases were extracted with ethyl acetate (1×50 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 100% ethyl acetate in heptane) to deliver 0.17 g (48.7%) of the title compound as white solid; MS (ESI) 450.0(M−H)−.

Workup

  1. customto give a light yellow suspension
  2. concentrationconcentrated in vacuo
  3. additionThe reaction mixture was poured into 100 mL ethyl acetate
  4. extractionextracted with 1 M HCl (1×25 mL) and brine (1×25 mL)
  5. extractionThe aqueous layer phases were extracted with ethyl acetate (1×50 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 40 g, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-eb44fb69af044e1693bd6aa1f71319ee
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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