HCID 18449632, compound → HCID 136166451, compound

HRID 1270450Notes

Reaction equation

HRID 1270450 reaction equation
[C:1]1([C:7]2([CH2:13][C:14]([NH:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19]([NH2:21])=[O:20])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.[OH-].[Na+]>[C:1]1([C:7]2([CH2:13][C:14]3[NH:21][C:19](=[O:20])[C:18]4[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:16]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 18449632HCID 18449632, compound

Product 1

HCID 136166451HCID 136166451, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The amide (73 mg, 0.217 mmol) in EtOH (1 mL) and 2N NaOH (1 mL) was heated at 80° C. for 1 h. The reaction mixture was concentrated, extracted with CH2Cl2 (3×) then dried over anhydrous sodium sulfate. Purification by flash chromatography (1:1, hexane-EtOAc) gave 2-(1-phenyl-cyclohexylmethyl)-3H-quinazolin-4-one (66 mg, 96%) as a white solid. Mass Spec [M+H]+=319.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. customPurification by flash chromatography (1:1, hexane-EtOAc)

Sources & evidence

ORD record
ord-5156904d521347098092dd9b5b104004
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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