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

HRID 875319Notes

Reaction equation

HRID 875319 reaction equation
Cl.C(OC([N:9]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[O:42][C:43]3[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:44]=3[N:45]=2)=[CH:37][CH:36]=1)[CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[N:15]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12][C:11]1=2)=O)(C)(C)C>O1CCOCC1>[Cl:50][C:47]1[CH:48]=[CH:49][C:43]2[O:42][C:41]([C:38]3[CH:39]=[CH:40][C:35]([CH2:34][O:33][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[CH2:26][CH2:25][NH:9][CH:10]4[CH2:19][CH2:18][CH2:17][C:16]5[N:15]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12][C:11]4=5)=[CH:36][CH:37]=3)=[N:45][C:44]=2[CH:46]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86709809Ethyl 5-{(tert-butoxycarbonyl)[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]-amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

Product 1

HCID 86709808Ethyl 5-{[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10 ml of a 4 N solution of hydrogen chloride in dioxane were added to 247 mg (0.36 mmol) of ethyl 5-{(tert-butoxycarbonyl)[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]-amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate (Enantiomer 1, Example 59A), and the mixture was stirred at room temperature for 4 h. The reaction solution was then concentrated to dryness and the residue was dried under high vacuum overnight. This gave 210 mg of the title compound as the hydrochloride in the form of a solid. This solid was taken up in 5 ml of THF, 0.13 ml of triethylamine was added and the mixture was stirred at room temperature for one hour. 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 then concentrated to dryness. This gave 149 mg (0.26 mmol, 72% of theory) of the target compound.

Workup

  1. concentrationThe reaction solution was then concentrated to dryness
  2. customthe residue was dried under high vacuum overnight
  3. addition0.13 ml of triethylamine was added
  4. stirringthe mixture was stirred at room temperature for one hour
  5. additionWater and ethyl acetate were then added to the mixture
  6. customthe phases were separated
  7. extractionThe aqueous phase was extracted twice with ethyl acetate
  8. dry with materialthe combined organic phases were then dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0a072c99aa8e4ca8aa1cf775cf226f7c
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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