Hydrochloric Acid → 2-(4-(4-Cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

HRID 927233Notes

Reaction equation

HRID 927233 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[N:16]([CH2:17][C:18]([O:20]CC)=[O:19])[C:15](=[O:23])[N:14]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[C:13]3[CH2:34][CH2:35][C:36](=[O:37])[C:12]2=3)=[C:7]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:6]=1)#[N:4].CO.Cl>O1CCCC1>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:15](=[O:23])[N:14]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=3)[C:13]3[CH2:34][CH2:35][C:36](=[O:37])[C:12]2=3)=[C:7]([S:38]([CH3:41])(=[O:39])=[O:40])[CH:6]=1)#[N:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 90310914Ethyl 2-(4-(4-Cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)-phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetate2×

Product 1

HCID 903109962-(4-(4-Cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (1.0 M, 10.0 mL, 10.0 mmol) is added to a solution of ethyl 2-(4-(4-cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetate (intermediate 29, 1.80 g, 3.20 mmol) in tetrahydrofuran (40 mL), and the mixture is stirred at room temperature over night. Another portion of aqueous sodium hydroxide solution (4.0 M, 2.0 mL, 8.0 mmol) and methanol (5.0 mL) is added, and mixture is stirred over night. Aqueous hydrogen chloride (1.0 M, 10 mL) is added, and the mixture is extracted with ethyl acetate. The organic layer is concentrated under reduced pressure, and the residue is purified reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 229 mg; ESI mass spectrum: [M+H]+=534; Retention time HPLC: 0.96 min (Z018_S04).

Workup

  1. stirringmixture is stirred over night
  2. extractionthe mixture is extracted with ethyl acetate
  3. concentrationThe organic layer is concentrated under reduced pressure
  4. customthe residue is purified
  5. custom0.96 min (Z018_S04)

Sources & evidence

ORD record
ord-b4f19a4afd86445fa2890638bd4821c7
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

Loading…