N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl) 1-propanol → 2-(2,6-difluorophenyl)-4-(3-trifluoromethylphenyl)-5,6-dihydro(4H)1,3-oxazine

HRID 1276215Notes

Reaction equation

HRID 1276215 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)[CH2:8][CH2:9]O)=[O:5].FC1C=CC=C(F)C=1C(NC(C1C=CC(Cl)=CC=1)CCO)=O>>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]1[O:5][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=2)[N:6]=1

Participants

3

Reactant 2

HCID 15790732N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl) 1-propanolHCID 22115241N-(2,6-difluorobenzoyl)-3-amino-3-(3-trifluoromethylphenyl)-1-propanol

Product 1

HCID 221152452-(2,6-difluorophenyl)-4-(3-trifluoromethylphenyl)-5,6-dihydro(4H)1,3-oxazineYield 71.3%

Procedure

The procedure is as for Example 85, but 4 g (11.1 mmol) of N-(2,6-difluorobenzoyl)-3-amino-3-(3-trifluoromethylphenyl)-1-propanol are employed instead of N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl)-1-propanol. 2.7 g (71.1%) of 2-(2,6-difluorophenyl)-4-(3-trifluoromethylphenyl)-5,6-dihydro(4H)1,3-oxazine are obtained as a colorless oil.

Sources & evidence

ORD record
ord-0935128c2f924cf89b184eed286c6a9c
Source dataset
uspto-grants-2000_12
Patent number
US06166010

Reaction notes

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