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

HRID 1276218Notes

Reaction equation

HRID 1276218 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[CH:13][C:12]=1[CH3:28])[CH2:8][CH2:9][OH:10])=O.FC1C=CC=C(F)C=1C(NC(C1C=CC(Cl)=CC=1)CCO)=O>>[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[C:4]1[O:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:27])[F:26])=[CH:19][CH:18]=3)=[CH:13][C:12]=2[CH3:28])[N:6]=1

Participants

3

Reactant 2

HCID 15790732N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl) 1-propanolHCID 22115242N-(2,6-difluorobenzoyl)-3-amino-3-(3-methyl-4'-trifluoromethoxybiphenyl-4-yl)-1-propanol

Product 1

HCID 221152442-(2,6-difluorophenyl)-4-(3-methyl-4'-trifluoromethoxybiphenyl-4-yl)-5,6-dihydro(4H)1,3-oxazineYield 64.5%

Procedure

The procedure is as for Example 85, but 5.0 g (10.8 mmol) of N-(2,6-difluorobenzoyl)-3-amino-3-(3-methyl-4'-trifluoromethoxybiphenyl-4-yl)-1-propanol are employed instead of N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl)-1-propanol. 3.1 g (64.5%) of 2-(2,6-difluorophenyl)-4-(3-methyl-4'-trifluoromethoxybiphenyl-4-yl)-5,6-dihydro(4H)1,3-oxazine are obtained as a colorless oil.

Sources & evidence

ORD record
ord-2903546e531b40c8bcaa1f6bcac4de71
Source dataset
uspto-grants-2000_12
Patent number
US06166010

Reaction notes

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