Hydrochloric Acid → 5-((4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)methyl)furan-2-carboxylic acid

HRID 517247Notes

Reaction equation

HRID 517247 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]2[O:38][C:37]([C:39]([O:41]C)=[O:40])=[CH:36][CH:35]=2)=[CH:7][CH:6]=1)#[N:4].Cl>O1CCCC1>[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]2[O:38][C:37]([C:39]([OH:41])=[O:40])=[CH:36][CH:35]=2)=[CH:9][CH:10]=1)#[N:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 86732367Methyl 5-((4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)methyl)furan-2-carboxylate

Product 1

HCID 867323685-((4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)methyl)furan-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (1.0 M, 100 μL, 100 μmol) is added to a solution of methyl 5-((4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)methyl)furan-2-carboxylate (example 28, 25 mg, 45 μmol) in tetrahydrofuran (2 mL), and the mixture is at room temperature over night. Another portion of aqueous sodium hydroxide solution (4 M, 100 μL, 400 μmol) is added and stiffing was continued over night. The mixture was acidified with aqueous hydrogen chloride solution to (1 M, 100 μL, 100 μmol) and purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 11 mg; ESI mass spectrum [M+H]+=536; Retention time HPLC: 0.91 min (Z018_S04).

Workup

  1. waitthe mixture is at room temperature over night
  2. waitstiffing was continued over night
  3. custompurified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  4. custom0.91 min (Z018_S04)

Sources & evidence

ORD record
ord-2d161b287ae5462c87616268f6efacc7
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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