Water → HCID 22405591, compound

HRID 441212Notes

Reaction equation

HRID 441212 reaction equation
[N+:1]([C:4]1[CH:39]=[CH:38][C:7]([C:8]([NH:10][C:11]2[C:12](=[O:37])[N:13]([CH2:23][C:24]([NH:26][CH:27]([CH:34]([CH3:36])[CH3:35])[C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[O:25])[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.O.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[C:12](=[O:37])[N:13]([CH2:23][C:24]([NH:26][CH:27]([CH:34]([CH3:36])[CH3:35])[C:28](=[O:33])[C:29]([F:32])([F:30])[F:31])=[O:25])[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)=[O:9])=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 22405608HCID 22405608, compound

Product 1

HCID 22405591HCID 22405591, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-[3-(4-nitrobenzoylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.38 g) in ethanol (20 mL), was added tin(II) chloride dihydrate (0.79 g). This mixture was heated to reflux for 1 h then cooled to ambient temperature. The reaction mixture was poured into water and the pH adjusted to 7-8 with saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate, and the organic extract washed (water, brine), dried (magnesium sulfate), and evaporated. The crude solid was triturated with diethyl ether:hexane (1:1), then further purified by chromatography, eluting with dichloromethane:methanol (gradient, 99.5:0.5, 99:1, 98.5:1.5), to give the title compound as a pale yellow solid; TLC: Rf =0.32, dichloromethane:methanol (98:2); MS: m/z=515(M+1).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 1 h
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. extractionthe organic extract
  5. washwashed (water, brine)
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customThe crude solid was triturated with diethyl ether:hexane (1:1)
  9. customfurther purified by chromatography
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-61335261be2242c48a59a4ddd32b12ed
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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