4-(Chloro(isocyanato)methyl)-3-fluorobenzonitrile → 4-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)-3-fluorobenzonitrile

HRID 927232Notes

Reaction equation

HRID 927232 reaction equation
Cl[CH:2]([N:12]=[C:13]=[O:14])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[F:11].[F:15][C:16]([F:31])([F:30])[C:17]1[CH:18]=[C:19]([NH:23][C:24]2[CH2:28][CH2:27][C:26](=[O:29])[CH:25]=2)[CH:20]=[CH:21][CH:22]=1>ClCCl>[O:14]=[C:13]1[N:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:30])[F:31])[CH:18]=2)[C:24]2[CH2:28][CH2:27][C:26](=[O:29])[C:25]=2[CH:2]([C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=2[F:11])[NH:12]1

Participants

4

Reactant 2

HCID 903108734-(Chloro(isocyanato)methyl)-3-fluorobenzonitrileHCID 903110573-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-one

Product 1

HCID 903110934-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)-3-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(chloro(isocyanato)methyl)-3-fluorobenzonitrile (Step 1, 3.05 g, 14.5 mmol) in dichloromethane (10 mL) is added to a solution of 3-(3-(trifluoromethyl)-phenylamino)cyclopent-2-enone (3.50 g, 14.5 mmol) in dichloromethane (10 mL), and the mixture is heated at reflux over night. All volatiles are removed under reduced pressure, and the residue is purified by reversed phase HPLC (Agilent ZORBAX™ SB-C18, gradient of acetonitrile in water, 0.1% formic acid). Yield: 474 mg; ESI mass spectrum [M+H]+=416; Retention time HPLC: 0.94 min (Z017_504). LB5FAI00917

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux over night
  3. customAll volatiles are removed 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. custom0.94 min (Z017_504)

Sources & evidence

ORD record
ord-94da1f01bfb24c70883426de48529bc8
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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