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Water → HCID 86732382, compound

HRID 517259
Notes
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Reaction equation

HRID 517259 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[H-].[Na+].[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:26]3[C:25](=[O:27])[CH2:24][CH2:23][CH2:22][C:21]=3[N:20]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=3)[C:19](=[O:38])[N:18]2[C:39](OC2C=CC([N+]([O-])=O)=CC=2)=[O:40])=[CH:13][CH:12]=1)#[N:10].O>O1CCCC1>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[C:26]3[C:25](=[O:27])[CH2:24][CH2:23][CH2:22][C:21]=3[N:20]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=3)[C:19](=[O:38])[N:18]2[C:39]([O:4][CH2:3][C:2]([CH3:6])([CH3:5])[CH3:1])=[O:40])=[CH:15][CH:16]=1)#[N:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6404Neopentyl alcohol3×HCID 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 86732382HCID 86732382, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,2-dimethyl-1-propanol (9 mg, 0.10 mmol) in dry tetrahydrofuran (1 mL) is cooled at −78° C. and treated with sodium hydride (60% in mineral oil, 5 mg, 0.11 mmol). After 20 min, a solution 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, 60 mg, 0.10 mmol) in tetrahydrofuran (1 mL) is added and the mixture is stirred for 5 h at room temperature. Another portion of 2,2-dimethyl-1-propanol (9 mg, 0.10 mmol) is added and the mixture is stirred over night. Another portion of 2,2-dimethyl-1-propanol (18 mg, 0.20 mmol) is added and the mixture is heated at 50° C. for 2 h. Water is added and the mixture is extracted with dichlormethane. The organic layer is concentrated under reduced it) pressure and the residue is purified by flash chromatography on silica (gradient cyclohexane to cyclohexane/ethyl acetate 1:1). Yield: 12 mg; ESI mass spectrum [M+H]+=526; Retention time HPLC: 0.76 min (X012_S01).

Workup

  1. stirringthe mixture is stirred over night
  2. temperaturethe mixture is heated at 50° C. for 2 h
  3. extractionthe mixture is extracted with dichlormethane
  4. concentrationThe organic layer is concentrated under reduced it) pressure
  5. customthe residue is purified by flash chromatography on silica (gradient cyclohexane to cyclohexane/ethyl acetate 1:1)
  6. custom0.76 min (X012_S01)

Sources & evidence

ORD record
ord-a021ef90c26c428295f5867d60508e9e
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115093B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes