Triethylamine → HCID 11642447, compound

HRID 1785955Notes

Reaction equation

HRID 1785955 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:11]2[CH:12]=[C:13]([C:16]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C@H:21]([NH2:28])[CH2:20][C@@H:19]3[CH3:29])=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(N(CC)CC)C.[C:47](OCC)(=[O:49])[CH3:48]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([N:6]1[C:11]2[CH:12]=[C:13]([C:16]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C@H:21]([N:28]([C:47](=[O:49])[CH3:48])[C:34]4[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=4)[CH2:20][C@@H:19]3[CH3:29])=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 742994-Chlorophenylboronic acidHCID 68922815HCID 68922815, compound

Product 1

HCID 11642447HCID 11642447, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S,4R)-6-(4-Amino-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid ethyl ester (470 mg, 1.18 mmol) in methylene chloride was added 4-chlorophenylboronic acid (368 mg, 2.36 mmol), triethylamine (1.31 mL, 9.42 mmol) and copper(II)acetate (429 mg, 2.36 mmol). The heterogeneous green mixture was stirred open to air for 1 hour and then warmed to 60° C. and stirred over night (14 hours). The mixture was then cooled to room temperature, poured into rapidly stirred ethyl acetate (150 mL); solids were removed by filtration through Celite®. The extracts were washed several times with water and then once with brine. The extracts were then dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (95% methylene chloride/5% ethyl acetate) to afford the aniline product as a yellow oil.

Workup

  1. stirringstirred over night (14 hours)
  2. temperatureThe mixture was then cooled to room temperature
  3. customsolids were removed by filtration through Celite®
  4. washThe extracts were washed several times with water
  5. dry with materialThe extracts were then dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica gel chromatography (95% methylene chloride/5% ethyl acetate)

Sources & evidence

ORD record
ord-47125615988f44448d32b8b079878f43
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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