Potassium Carbonate → HCID 86746854, compound

HRID 248925Notes

Reaction equation

HRID 248925 reaction equation
[CH2:1]1[O:19][C:4]([CH2:17][CH3:18])([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[C:7]=2[NH2:16])[O:3][CH2:2]1.[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=1)#[N:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:2]1[O:3][C:4]([CH2:17][CH3:18])([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[C:7]=2[NH:16][CH2:34][C:31]2[CH:30]=[CH:29][C:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[C:20]#[N:21])=[CH:33][CH:32]=2)[O:19][CH2:1]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 57120211HCID 57120211, compound

Product 1

HCID 86746854HCID 86746854, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-amino-3-methoxycarbonylphenyl)butan-2-one ethylene ketal (T) (0.7 g) (prepared, e.g., as described in Preparation 14), 2'-(cyano)biphenyl-4-yl-methylbromide (0.826 g) and potassium carbonate (0.41 g) in dimethylformamide (20 ml) was heated at 80°-90° C. for 16 hours under an inert atmosphere. The reaction mixture was concentrated under reduced pressure, and the residue obtained was diluted with ethyl acetate (100 ml), washed twice with cold water, and then brine. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel, eluting with 20% ethyl acetate/hexane, to give 1-[2-(2"-cyanobiphenyl-4'-ylmethylamino)-3-methoxycarbonylphenyl]butan-2-one ethylene ketal (0.52 g), a compound of Formula (U), as an oil.

Workup

  1. temperaturewas heated at 80°-90° C. for 16 hours under an inert atmosphere
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue obtained
  4. washwashed twice with cold water
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed on silica gel
  7. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c3ad0616b56147bb977479271684cda0
Source dataset
uspto-grants-1993_05
Patent number
US05212195

Reaction notes

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