4-(4-Cyano-2-(methylsulfonyl)phenyl)-N-methyl-2,5-dioxo-1-(3-(trifluoromethyl)-phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxamide → 4-(4-Cyano-2-(methylsulfonyl)phenyl)-1-(3-(difluoromethyl)phenyl)-N-methyl-2,5-dioxo-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxamide

HRID 517266Notes

Reaction equation

HRID 517266 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26](F)([F:28])[F:27])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([NH:33][CH3:34])=[O:32])=[C:5]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:4]=1)#[N:2].C(C1C=CC(C2C3C(=O)CCCC=3N(C3C=CC=C(C(F)F)C=3)C(=O)N2C(OC2C=CC([N+]([O-])=O)=CC=2)=O)=C(S(C)(=O)=O)C=1)#N>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([F:27])[F:28])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([NH:33][CH3:34])=[O:32])=[C:5]([S:35]([CH3:38])(=[O:36])=[O:37])[CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 867323884-(4-Cyano-2-(methylsulfonyl)phenyl)-N-methyl-2,5-dioxo-1-(3-(trifluoromethyl)-phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxamideHCID 867323914-nitrophenyl 4-(4-cyano-2-(methylsulfonyl)-phenyl)-1-(3-(difluoromethyl)phenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxylate2×

Product 1

HCID 867323904-(4-Cyano-2-(methylsulfonyl)phenyl)-1-(3-(difluoromethyl)phenyl)-N-methyl-2,5-dioxo-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxamide

Procedure

The title compound is prepared in analogy to 4-(4-cyano-2-(methylsulfonyl)-phenyl)-N-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxamide (example 47), using 4-nitrophenyl 4-(4-cyano-2-(methylsulfonyl)-phenyl)-1-(3-(difluoromethyl)phenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxylate (intermediate 39, 16 mg, 25 μmol), as starting material. Yield: 9 mg, ESI mass spectrum [M+H]+=529; Retention time HPLC: 0.97 min (Z017_S04).

Workup

  1. custom0.97 min (Z017_S04)

Sources & evidence

ORD record
ord-2b8c915f9a7b4080ada9133e86d8213d
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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