3-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-one → 4-(4-bromo-2-(methylsulfonyl)phenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopentapyrimidine-2,5-dione

HRID 927194Notes

Reaction equation

HRID 927194 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH2:14][CH2:13][C:12](=[O:15])[CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25](Cl)[N:26]=[C:27]=[O:28])=[C:21]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:20]=1>ClCCl>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[NH:26][C:27](=[O:28])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:4]=3)[C:10]3[CH2:14][CH2:13][C:12](=[O:15])[C:11]2=3)=[C:21]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:20]=1

Participants

4

Reactant 2

HCID 903110573-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-oneHCID 903110884-Bromo-1-(chloro(isocyanato)methyl)-2-(methylsulfonyl)benzene

Product 1

HCID 903110044-(4-bromo-2-(methylsulfonyl)phenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopentapyrimidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-(Trifluoromethyl)phenylamino)cyclopent-2-enone (234 mg, 0.97 mmol) is added to a solution of 4-bromo-1-(chloro(isocyanato)methyl)-2-(methylsulfonyl)benzene (Step 1, 945 mg, 2.91 mmol) in dichloromethane (10 mL). The mixture is heated at reflux over night and then concentrated under reduced pressure. The residue is purified by reversed phase HPLC (Agilent ZORBAX™ SB—C18, gradient of acetonitrile in water, 0.1% formic acid). Yield: 110 mg; ESI mass spectrum: ESI mass spectrum: [(79Br)-M+H]+=529, [(81Br)-M+H]+=531; Retention time HPLC: 1.21 min (Z017_S04).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux over night
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by reversed phase HPLC (Agilent ZORBAX™ SB—C18, gradient of acetonitrile in water, 0.1% formic acid)
  5. custom1.21 min (Z017_S04)

Sources & evidence

ORD record
ord-d1c1d80ae4bc45a7aa95938feeec1b47
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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