Ethyl Acetate → HCID 57646682, compound

HRID 1452519Notes

Reaction equation

HRID 1452519 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:9]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:10](=[O:22])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][C@H:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:11]1[CH:12]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:38][C@H:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH3:30])[CH:7]=2)[N:9]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:10]1=[O:22])#[N:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 758181-Phenethylamine, (-)-HCID 23020386HCID 23020386, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 57646682HCID 57646682, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

50 mg of 4-(2-chloropyridin-4-yl)-3-(4-fluorophenyl)-1-(2-cyanobenzy 1)-4-imidazolin-2-one (a compound of Reference Example 1 (6)), 79 μl of (S)-(−)-α-methylbenzylamine, 5.5 mg of palladium acetate, 15 mg of 2,2′-bis (diphenylphsophino)-1,1′-binaphthyl and 17 mg of sodium t-butoxide were suspended in 1 ml of toluene, and the mixture was stirred at 70° C. for 18 hours, under nitrogen flow. The reaction mixture was diluted by ethyl acetate, and insoluble matter was removed by filtration through Celite. To the filtrate was added 6N hydrochloric acid, and after separation, an aqueous layer was made alkaline with aqueous sodium bicarbonate solution. The mixture was extracted with chloroform, washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1: 2), to give 38 mg of the title compound as colorless powder.

Workup

  1. customwas removed by filtration through Celite
  2. additionTo the filtrate was added 6N hydrochloric acid
  3. customafter separation
  4. extractionThe mixture was extracted with chloroform
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1: 2)

Sources & evidence

ORD record
ord-7aba503165ef4275803fd1085c4b2664
Source dataset
uspto-grants-2009_01
Patent number
US07473695B2

Reaction notes

Loading…