Diisopropylethylamine → HCID 57595517, compound

HRID 1786080Notes

Reaction equation

HRID 1786080 reaction equation
Cl[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:5]=1)=[O:3].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]([C@H:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][C@@H:33]([CH3:41])[CH2:32]2)[C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:17][O:16][C:14](=[O:15])[C:13]([CH3:19])([CH3:18])[CH2:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([N:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:31]([N:27]([C:28](=[O:30])[CH3:29])[C:24]3[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][CH:25]=3)[CH2:32][C@@H:33]2[CH3:41])=[O:3])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57421380HCID 57421380, compoundHCID 57595495HCID 57595495, compound

Product 1

HCID 57595517HCID 57595517, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the prepared methyl 5-[4-(chlorocarbonyl)phenyl]-2,2-dimethylpentanoate (2.9 mmol, 1.0 eq.) was added a solution of N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)acetamide (754 mg, 2.4 mmol, 0.83 eq.) in methylene chloride (8 ml) followed by diisopropylethylamine (505 ul, 2.9 mmol, 1.0 eq.) and reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated and the residue dissolved in ethyl acetate and washed with water, brine, and then dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (ethyl acetate/hexane: ⅓ to ½ gradient) to afford 5-(4-{(2S,4R)-4-[acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-2,2-dimethyl-pentanoic acid methyl ester (675 mg, 50%).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography (ethyl acetate/hexane: ⅓ to ½ gradient)

Sources & evidence

ORD record
ord-0dc935bc31f744fd9decd418eac7e97d
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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