Diisopropylethylamine → HCID 57595487, compound

HRID 1785987Notes

Reaction equation

HRID 1785987 reaction equation
[C:1]([O:4][CH2:5][C:6]([N:8]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C@@H:11]([CH3:19])[CH2:10]1)=[O:7])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:37]([C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][C:48]([CH3:54])([CH3:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:41][CH:40]=1)=[O:38]>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]([N:8]([C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:37]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][C:48]([CH3:54])([CH3:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:41][CH:40]=2)=[O:38])[C@@H:11]([CH3:19])[CH2:10]1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57421380HCID 57421380, compoundHCID 68921124HCID 68921124, compound

Product 1

HCID 57595487HCID 57595487, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{(4-chlorophenyl)[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-oxoethyl acetate (170 mg, 0.45 mmol, 1 equ.) in methylene chloride (2.0 mL) at room temperature was added diisopropylethylamine (127 uL, 0.73 mmol, 1.60 equ.) followed by methyl 5-[4-(chlorocarbonyl)phenyl]-2,2-dimethylpentanoate (196 mg, 0.73 mmol, 1.60 equ.). The reaction was stirred over night at room temperature. The mixture was concentrated, then poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, filtered dried and concentrated. The crude residue was purified by silica gel chromatography (ethyl acetate/hexane 25/75 to 1:1 gradient) to afford the pure methyl 5-(4-{[(2S,4R)-4-[[(acetyloxy)acetyl](4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (110 mg, 40%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customdried
  8. concentrationconcentrated
  9. customThe crude residue was purified by silica gel chromatography (ethyl acetate/hexane 25/75 to 1:1 gradient)

Sources & evidence

ORD record
ord-d66277e98d1f4a59a5cad9023b6c3b9e
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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