Diphenyl N-Cyanocarbonimidate → HCID 178512248, compound

HRID 2104586Notes

Reaction equation

HRID 2104586 reaction equation
C1C=CC(O[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]#[N:11])=CC=1.[NH2:19][C:20]1[CH:21]=[C:22]([C:26]2[C:35]3[C:30](=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:32]=[CH:33][CH:34]=3)[N:29]=[CH:28][C:27]=2[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:41])[CH:23]=[CH:24][CH:25]=1>C(#N)C>[C:40]([C:27]1[CH:28]=[N:29][C:30]2[C:35]([C:26]=1[C:22]1[CH:21]=[C:20]([NH:19][C:8](=[N:9][C:10]#[N:11])[O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:25]=[CH:24][CH:23]=1)=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([F:39])([F:37])[F:38])(=[O:41])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 11326798[4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Product 1

HCID 178512248HCID 178512248, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of diphenyl cyanocarbonimidate (0.6 g, 2.52 mmol) and [4-(3-amino-phenyl)-8-trifluoromethyl-quinolin-3-yl]-phenyl-methanone (0.1 g, 0.26 mmol) in 30 mL of acetonitrile was refluxed for 3 days. Removal of solvent under reduced pressure gave a crude product that was purified by silica gel chromatography eluting with ethyl acetate/hexanes (5% to 30%) to give 65 mg (47%) of the title compound as an off-white solid. MS (ES) m/z 534.9.

Workup

  1. temperaturewas refluxed for 3 days
  2. customRemoval of solvent under reduced pressure
  3. customgave a crude product that
  4. customwas purified by silica gel chromatography
  5. washeluting with ethyl acetate/hexanes (5% to 30%)

Sources & evidence

ORD record
ord-7b2c7d660a344afc846f05f8ab4cb023
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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