Methylamine → 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

HRID 517263Notes

Reaction equation

HRID 517263 reaction equation
[CH3:1][NH2:2].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:20]3[C:19](=[O:21])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:13](=[O:32])[N:12]2[C:33](OC2C=CC([N+]([O-])=O)=CC=2)=[O:34])=[C:7]([S:45]([CH3:48])(=[O:47])=[O:46])[CH:6]=1)#[N:4]>C(#N)C>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:20]3[C:19](=[O:21])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[CH:23]=3)[C:13](=[O:32])[N:12]2[C:33]([NH:2][CH3:1])=[O:34])=[C:7]([S:45]([CH3:48])(=[O:46])=[O:47])[CH:6]=1)#[N:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86732327HCID 86732327, compound2×

Product 1

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)-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methylamine (2.0 M in tetrahydrofuran, 69 μL, 138 μmol) is added to a solution of 4-nitrophenyl 4-(4-cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxylate (intermediate 38, 30 mg, 46 μmol) in acetonitrile (1 mL). The mixture is stirred at room temperature for 20 min and purified by reversed phase HPLC (Agilent ZORBAX™ SB-C18, gradient of acetonitrile in water, 0.15% formic acid). Yield: 22 mg; ESI mass spectrum M+H]+=547, Retention time HPLC: 1.01 min (Z017_S04).

Workup

  1. custompurified by reversed phase HPLC (Agilent ZORBAX™ SB-C18, gradient of acetonitrile in water, 0.15% formic acid)
  2. custom1.01 min (Z017_S04)

Sources & evidence

ORD record
ord-c97bea9c7ae5400198a711c814f69e1b
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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