Potassium Carbonate → HCID 57595536, compound

HRID 1786035Notes

Reaction equation

HRID 1786035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C@@H:14]([CH3:31])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:38][O:39][C:40](=[O:47])[C:41]([CH3:46])([CH3:45])[CH2:42][CH2:43]Br>CN(C=O)C>[CH3:38][O:39][C:40](=[O:47])[C:41]([CH3:46])([CH3:45])[CH2:42][CH2:43][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:12]([N:8]([C:9](=[O:11])[CH3:10])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:13][C@@H:14]2[CH3:31])=[O:30])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14928877Butanoic acid, 4-bromo-2,2-dimethyl-, methyl esterHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 57595536HCID 57595536, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.126 g, 0.242 mmol) was dissolved in 3 ml DMF at room temperature and K2CO3 (0.267 g, 1.94 mmol) was added. 4-Bromo-2,2-dimethyl-butyric acid methyl ester (0.202 g, 0.969 mmol, prepared according to the procedure from Tetrahedron 1994, 50(32), 9825-30) was added and the reaction was allowed to heat to 80° C. overnight. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (50% EtOAc/50% Hexane) to afford the (2S,4R)-4-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2,2-dimethyl-butyric acid methyl ester (0.105 g, 77%).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. customThe crude residue was purified by silica gel chromatography (50% EtOAc/50% Hexane)

Sources & evidence

ORD record
ord-a42dd5c064554bc2866a792dbe662f81
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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