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

HRID 1276216Notes

Reaction equation

HRID 1276216 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]([CH3:20])([CH3:19])[CH3:18])[CH:12]=1)[CH2:8][CH2:9][OH:10])=O.FC1C=CC=C(F)C=1C(NC(C1C=CC(Cl)=CC=1)CCO)=O>>[F:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:2]([F:1])[C:3]=1[C:4]1[O:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([CH3:19])([CH3:18])[CH3:20])[CH:12]=2)[N:6]=1

Participants

3

Reactant 2

HCID 15790732N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl) 1-propanolHCID 22115246N-(2,6-difluorobenzoyl)-3-amino-3-(3-tert-butylphenyl)-1-propanol

Product 1

HCID 221152372-(2,6-difluorophenyl)-4-(3-tert-butylphenyl)-5,6-dihydro(4H)1,3-oxazineYield 68.6%

Procedure

The procedure is as for Example 85, but 4.0 g (11.5 mmol) of N-(2,6-difluorobenzoyl)-3-amino-3-(3-tert-butylphenyl)-1-propanol are employed instead of N-(2,6-difluorobenzoyl)-3-amino-3-(4-chlorophenyl) 1-propanol. 2.6 g (68.6%) of 2-(2,6-difluorophenyl)-4-(3-tert-butylphenyl)-5,6-dihydro(4H)1,3- oxazine are obtained as a colorless oil.

Sources & evidence

ORD record
ord-85699c27bf744c7cbf80c19b5d90ae80
Source dataset
uspto-grants-2000_12
Patent number
US06166010

Reaction notes

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