Water → HCID 86732371, compound

HRID 517250Notes

Reaction equation

HRID 517250 reaction equation
[OH-].[Na+].[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[CH2:33][C:34]([O:36]C)=[O:35])=[CH:7][CH:6]=1)#[N:4].O>O1CCOCC1>[C:3]([C:5]1[CH:6]=[CH:7][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:30])([F:31])[F:29])[CH:23]=3)[C:13](=[O:32])[N:12]2[CH2:33][C:34]([OH:36])=[O:35])=[CH:9][CH:10]=1)#[N:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86732370HCID 86732370, compound

Product 1

HCID 86732371HCID 86732371, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous sodium hydroxide solution (1 M, 7.27 mL, 7.27 mmol) is added to a solution of methyl 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)acetate (example 31, 1.76 g, 3.64 mmol) in 1,4-dioxane (15 mL) and the mixture is stirred at room temperature for 1 h. Water (80 mL) is added and the mixture is extracted twice with diethyl ether. The organic phase is discarded and the aqueous phase is acidified with aqueous hydrogen chloride (1 M) and extracted three times with diethyl ether. The combined organic layers are washed with water and saturated aqueous sodium chloride, and concentrated under reduced pressure. Yield: 1.69 g; ESI mass spectrum [M+H]+=470; Retention time: 0.88 min (Z018_S04).

Workup

  1. extractionthe mixture is extracted twice with diethyl ether
  2. extractionextracted three times with diethyl ether
  3. washThe combined organic layers are washed with water and saturated aqueous sodium chloride
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be621a18b7814f98b1b06d5c5d791999
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

Loading…