(S)-4-(3-Methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile → 4-(1-(3-(Difluoromethyl)phenyl)-3-methyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile

HRID 517265Notes

Reaction equation

HRID 517265 reaction equation
[CH3:1][N:2]1[C@H:11]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[S:20]([CH3:23])(=[O:22])=[O:21])[C:10]2[C:9](=[O:24])[CH2:8][CH2:7][CH2:6][C:5]=2[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31](F)([F:33])[F:32])[CH:26]=2)[C:3]1=[O:35].FC(F)C1C=C(N2C3CCCC(=O)C=3C(C3C=CC(C#N)=CC=3S(C)(=O)=O)NC2=O)C=CC=1>>[F:33][CH:31]([F:32])[C:27]1[CH:26]=[C:25]([N:4]2[C:5]3[CH2:6][CH2:7][CH2:8][C:9](=[O:24])[C:10]=3[CH:11]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=3[S:20]([CH3:23])(=[O:22])=[O:21])[N:2]([CH3:1])[C:3]2=[O:35])[CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 86270876(S)-4-(3-Methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrileHCID 86732360HCID 86732360, compound

Product 1

HCID 867323894-(1-(3-(Difluoromethyl)phenyl)-3-methyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile

Procedure

The title compound is prepared in analogy to (S)-4-(3-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile (example 48), using 4-(1-(3-(difluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile (example 19, 60 mg, 0.13 mmol) as starting material. Yield: 20 mg, ESI mass spectrum [M+H]+=486; Retention time HPLC: 0.99 min (Z017_S04).

Workup

  1. custom0.99 min (Z017_S04)

Sources & evidence

ORD record
ord-6df6e7908ca944c08bfb7e5a957dc3b9
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

Loading…