Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methylene}piperidine-1-carboxylate → Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperidine-1-carboxylate

HRID 394115Notes

Reaction equation

HRID 394115 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH:18]=[C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:40])[N:13]2[C:32]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:39]>C(OCC)(=O)C.O.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:40])[N:13]2[C:32]1[C:33]([Cl:39])=[CH:34][CH:35]=[CH:36][C:37]=1[Cl:38]

Participants

4

Reactant 1

HCID 22648188Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methylene}piperidine-1-carboxylate

Product 1

HCID 22647967Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methylene}piperidine-1-carboxylate (EXAMPLE AAA18, STEP C, 150 mg, 0.25 mmol) in ethyl acetate (4 mL) was purged and filled with nitrogen. To this was added platinum (IV) oxide hydrate (30 mg, 20% weight). The mixture was evacuated and filled with hydrogen via balloon. Then the reaction was stirred at rt under hydrogen for 1 h, filtered through celite and rinsed with ethyl acetate and methanol. Removal of the solvent provided tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperidine-1-carboxylate as a white solid used directly for the next step.

Workup

  1. additionfilled with nitrogen
  2. customThe mixture was evacuated
  3. additionfilled with hydrogen via balloon
  4. filtrationfiltered through celite
  5. washrinsed with ethyl acetate and methanol
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-7336037e33ca451ba379123915055fd9
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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