(3-Trifluoromethylphenyl)urea → HCID 59684815, compound

HRID 421794Notes

Reaction equation

HRID 421794 reaction equation
[CH2:1]([O:8][CH:9]([CH3:16])[C:10](=[O:15])[CH2:11][C:12](=O)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)#[N:18].[F:27][C:28]([F:40])([F:39])[C:29]1[CH:30]=[C:31]([NH:35][C:36]([NH2:38])=[O:37])[CH:32]=[CH:33][CH:34]=1>O1CCCC1>[CH2:1]([O:8][CH:9]([CH3:16])[C:10]([C:11]1[CH:23]([C:22]2[CH:25]=[CH:26][C:19]([C:17]#[N:18])=[CH:20][CH:21]=2)[NH:38][C:36](=[O:37])[N:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:39])([F:40])[F:27])[CH:30]=2)[C:12]=1[CH3:13])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 59684861HCID 59684861, compound

Product 1

HCID 59684815HCID 59684815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(benzyloxy)hexane-2,4-dione (250 mg, 1.13 mmol; Example 8A), 4-cyanobenzaldehyde (149 mg, 1.13 mmol) and N-[3-(trifluoromethyl)phenyl]urea (232 mg, 1.13 mmol) in tetrahydrofuran (5 ml) is added polyphosphoric acid ethyl ester (700 mg). After 16 hours, the reaction solution is purified directly by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10). The fractions containing product are concentrated and again purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10).

Workup

  1. customthe reaction solution is purified directly by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10)
  2. additionThe fractions containing product
  3. concentrationare concentrated
  4. customagain purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10)

Sources & evidence

ORD record
ord-3b95796cb36a4225a56034d4259e87ed
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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