4-(Amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-chloro-benzonitrile hydrochloride → 3-Chloro-4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

HRID 517271Notes

Reaction equation

HRID 517271 reaction equation
[O:1]=[C:2]1[NH:11][CH:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2C)[C:9]2[C:8](=[O:21])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.Cl.NC(C1C(=O)CCCC=1NC1C=CC=C(C(F)(F)F)C=1)C1C=CC(C#N)=CC=1[Cl:43]>>[Cl:43][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:12]=1[CH:10]1[C:9]2[C:8](=[O:21])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:2](=[O:1])[NH:11]1)[C:16]#[N:17]

Participants

3

Reactant 2

HCID 867323434-(Amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-chloro-benzonitrile hydrochloride2×HCID 867323954-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-methylbenzonitrile

Product 1

HCID 867323963-Chloro-4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

Procedure

The title compound is prepared in analogy to 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-methylbenzonitrile (example 55), using 4-(amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-chloro-benzonitrile hydrochloride (intermediate 54, 620 mg, 1.36 mmol) as starting material. Yield: 191 mg; ESI mass spectrum [M+H]+=446; Retention time HPLC: 0.65 min (X012_S01).

Workup

  1. custom0.65 min (X012_S01)

Sources & evidence

ORD record
ord-026d751ccf0548159b774ceb76cc5cd0
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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