Water → Ethyl 5-{[2-(2-{[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875321Notes

Reaction equation

HRID 875321 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:43]=[CH:42][C:15]([CH2:16][O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH2:24][CH2:25][NH:26][CH:27]4[CH2:36][CH2:35][CH2:34][C:33]5[N:32]=[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:30]=[CH:29][C:28]4=5)=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:44]=1.C(N(CC)CC)C.O.C(OCC)(=O)C>C1COCC1>[CH3:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH2:16][O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH2:24][CH2:25][NH:26][CH:27]4[CH2:36][CH2:35][CH2:34][C:33]5[N:32]=[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:30]=[CH:29][C:28]4=5)=[CH:42][CH:43]=3)=[N:9][C:8]=2[CH:44]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86709804Ethyl 5-{[2-(2-{[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride

Product 1

HCID 86709805Ethyl 5-{[2-(2-{[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.8 g (5.99 mmol) of ethyl 5-{[2-(2-{[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]-amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride (Enantiomer 1, Example 27A) were dissolved in 50 ml of THF, 2.5 ml of triethylamine were added and the mixture was stirred at room temperature for 1 h. Water and ethyl acetate were then added to the mixture, and the phases were separated. The aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were then dried over magnesium sulphate, filtered and concentrated to dryness. This gave 2.48 g (4.42 mmol, 74% of theory) of the target compound.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases were then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-776f716c0388458282c3a283b0d0f4b7
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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