2-Chloro-5-(chloro(isocyanato)methyl)pyridine → 4-(6-Chloropyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-2,5-dione

HRID 927195Notes

Reaction equation

HRID 927195 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.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25](Cl)[N:26]=[C:27]=[O:28])=[CH:21][N:20]=1>ClCCl>[Cl:18][C:19]1[N:20]=[CH:21][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)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 903110302-Chloro-5-(chloro(isocyanato)methyl)pyridine2×HCID 903110573-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-one

Product 1

HCID 903108714-(6-Chloropyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(3-(trifluoromethyl)phenylamino)cyclopent-2-enone (900 mg, 3.73 mmol) in dichloromethane (8 mL) is added dropweise to a solution of 2-chloro-5-(chloro(iso-cyanato)methyl)pyridine (intermediate 10, 757 mg, 3.73 mmol) in dichloromethane (7 mL). The mixture is stirred at room temperature for 2 h and concentrated, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 160 mg; ESI mass spectrum [M+H]+=408; Retention time HPLC: 0.98 min (V011_S01).

Workup

  1. concentrationconcentrated
  2. customthe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  3. custom0.98 min (V011_S01)

Sources & evidence

ORD record
ord-95cb6745b6eb45009303b2e2d69437ea
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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