P-Anisidine → HCID 22137667, compound

HRID 1827312Notes

Reaction equation

HRID 1827312 reaction equation
Br[CH:2]([C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](=[O:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[CH3:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>C(N(CC)CC)C>[CH3:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][CH:2]([C:4]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12](=[O:21])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH3:3])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 4353710HCID 4353710, compound

Product 1

HCID 22137667HCID 22137667, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Ethyl-3-benzyl-quinazolin-4-one is prepared following the procedure set forth in part (A) above, but substituting N-benzyl-2-(propanoylamino)-benzamide for N-(1-benzoylethyl)-2-(formylamino)-benzamide (“Compound E”). Compound E is brominated by heating in acetic acid with bromine to provide 2-(1-bromoethyl)-3-benzyl-quinazolin-4-one (“Compound F”). Compound F is treated with 4-methoxy-aniline in triethylamine to provide 2-(1-(4-methoxyphenylamino)ethyl)-3-benzyl-quinazolin-4-one (“Compound G”). Compound G is then acylated with benzoyl chloride to provide 2-(1-(N-benzoyl-N-(4-methoxyphenyl)-aminoethyl)-3-benzyl-quinazolin-4-one.

Sources & evidence

ORD record
ord-2bdfa055382e4b6b99ac6a1a90267c91
Source dataset
uspto-grants-2006_05
Patent number
US07053216B2

Reaction notes

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