(3-Trifluoromethylphenyl)urea → HCID 59684776, compound

HRID 421805Notes

Reaction equation

HRID 421805 reaction equation
[C:1]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)#[N:24].[F:33][C:34]([F:46])([F:45])[C:35]1[CH:36]=[C:37]([NH:41][C:42]([NH2:44])=[O:43])[CH:38]=[CH:39][CH:40]=1>C(OC)(C)(C)C>[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]2[C:2]([C:1]([CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][N:8]3[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[O:6])=[C:3]([CH3:5])[N:41]([C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([C:34]([F:45])([F:46])[F:33])[CH:36]=3)[C:42](=[O:43])[NH:44]2)=[CH:27][CH:26]=1)#[N:24]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 59684791HCID 59684791, compound

Product 1

HCID 59684776HCID 59684776, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A stirred mixture of benzyl 2-acetoacetylpiperidine-1-carboxylate (Example 10A) (1.74 g, 5.74 mmol), 4-cyanobenzaldehyde (752 mg, 5.74 mmol), N-[3-(trifluoromethyl)phenyl]urea (976 mg, 4.78 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide anhydride (6.1 g, 9.5 mmol) in methyl tert.-butyl ether (44 ml) is refluxed overnight (16 h). The product is extracted with methyl tert.-butyl ether (300 ml), washed with aq. saturated sodium bicarbonate solution (200 ml), dried with anhydrous magnesium sulfate, filtered and concentrated. The residue is chromatographed with silica gel 60 using cyclohexane/ethyl acetate as eluent.

Workup

  1. temperatureis refluxed overnight (16 h)
  2. extractionThe product is extracted with methyl tert.-butyl ether (300 ml)
  3. washwashed with aq. saturated sodium bicarbonate solution (200 ml)
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed with silica gel 60 using cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-d2d2fcb49354409faeff816dfe9363a1
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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