Dimethylamine → HCID 86732379, compound

HRID 517256Notes

Reaction equation

HRID 517256 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:29])([F:28])[F:27])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([O:33]C2C=CC([N+]([O-])=O)=CC=2)=O)=[CH:5][CH:4]=1)#[N:2].[CH3:43][NH:44][CH3:45]>C(#N)C>[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:27])([F:28])[F:29])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([N:44]([CH3:45])[CH3:43])=[O:33])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 867323254-Nitrophenyl 4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxylate2×

Product 1

HCID 86732379HCID 86732379, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-nitrophenyl 4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxylate (intermediate 37, 51 mg, 8 μmol) and dimethylamine (2.0 M in tetrahydrofuran, 220 μL, 440 μmol) in acetonitrile (1.5 mL) is stirred at room temperature for 30 h and purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 14 mg; ESI mass spectrum [M+H]+=483; Retention time HPLC: 1.03 min (Z018_S04).

Workup

  1. custompurified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  2. custom1.03 min (Z018_S04)

Sources & evidence

ORD record
ord-786bc31b6da94ef9862365004ebd693f
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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