Phenethylamine → 3-(p-Tolyl)-1,4-dihydro-4-oxo-5-phenethylamino-1,6-naphthyridine

HRID 1044323Notes

Reaction equation

HRID 1044323 reaction equation
F[C:2](F)(F)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[N:15][C:16]=3[NH:20]C3C=CC(Cl)=CC=3)[NH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](OCC)=O)=[CH:33][CH:32]=1.FC(F)(F)C1C=CC(CC(OCC)=O)=CC=1.C(N)CC1C=CC=CC=1.ClC1C=CC(N)=CC=1>>[C:3]1([CH3:2])[CH:8]=[CH:7][C:6]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[N:15][C:16]=3[NH:20][CH2:38][CH2:37][C:34]3[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=3)[NH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 1001PhenethylamineHCID 78124-ChloroanilineHCID 84177Ethyl (4-chlorophenyl)acetateHCID 14134124Ethyl (4-(trifluoromethyl)phenyl)acetateHCID 468478053-(4-Trifluoromethylphenyl)-1,4-dihydro-4-oxo-5-(4-chlorophenylamino)-1,6-naphthyridine

Product 1

HCID 468476093-(p-Tolyl)-1,4-dihydro-4-oxo-5-phenethylamino-1,6-naphthyridine

Procedure

3-(4-Trifluoromethylphenyl)-1,4-dihydro-4-oxo-5-(4-chlorophenylamino)-1,6-naphthyridine The title compound was prepared as described in Example 1 above except that ethyl (4-chlorophenyl)acetate was replaced with ethyl (4-trifluoromethyl-phenyl)acetate and phenethylamine was replaced with 4-chloroaniline. MS 416 (M+1)+.

Sources & evidence

ORD record
ord-0c818d7e4a9949b59602ec8d2c717033
Source dataset
uspto-grants-2013_10
Patent number
US08563579B2

Reaction notes

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