1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-1H-quinolin-2-one

HRID 858999Notes

Reaction equation

HRID 858999 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[OH:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25](=[O:29])[NH:26]2)=[CH:21][CH:20]=1.N12CCCN=C1CCCCC2>CC#N>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([O:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]=[CH:24][C:25](=[O:29])[NH:26]4)=[CH:21][CH:20]=3)[CH:7]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109757877-HydroxycarbostyrilHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Product 1

HCID 104075877-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared analogous to the methods used in Example 32(e) using 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (0.50 g, 1.9 mmol), 7-hydroxy-1H-quinolin-2-one (0.37 g, 2.3 mmol, prepared according to Synthesis 1997, 87–90) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.35 mL, 2.3 mmol, Aldrich) in CH3CN (40 mL). Purification by flash chromatography (0→2.5% MeOH/CH2Cl2) afforded the title compound as an off-white powder. Mp 288° C. MS (ESI, pos. ion) n/z: 384 (M+1).

Workup

  1. customThe title compound was prepared analogous to the methods
  2. customPurification by flash chromatography (0→2.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5768c763e1824f8683ed264aef5c217c
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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