Water → HCID 86732381, compound

HRID 517258Notes

Reaction equation

HRID 517258 reaction equation
[CH3:1][O:2]CCO.[H-].[Na+].[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=3[N:19]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[C:18](=[O:37])[N:17]2[C:38]([O:40][C:41]2[CH:46]=CC([N+]([O-])=O)=CC=2)=[O:39])=[CH:12][CH:11]=1)#[N:9].O>O1CCCC1>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=3[N:19]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=3)[C:18](=[O:37])[N:17]2[C:38]([O:40][CH2:41][CH2:46][O:2][CH3:1])=[O:39])=[CH:14][CH:15]=1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 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 86732381HCID 86732381, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methoxyethanol (7 μL, 89 μmol) in dry tetrahydrofuran (500 μL) is cooled at 78° C. and treated with sodium hydride (60% in mineral oil, 9 mg, 0.14 mmol). After 30 min, 4-nitrophenyl 4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxylate (intermediate 37, 50 mg, 87 μmol) is added and the mixture is stirred at room temperature for 2 h. Water is added and the mixture is purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 8 mg; ESI mass spectrum [M+H]+=514; Retention time HPLC: 0.64 min (X012_S01).

Workup

  1. customthe mixture is purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  2. custom0.64 min (X012_S01)

Sources & evidence

ORD record
ord-1d03c27f55014e478cdef3b4cf6bb706
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

Loading…