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

HRID 875331Notes

Reaction equation

HRID 875331 reaction equation
[ClH:1].C(OC([N:9]([CH2:25][CH2:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[O:43][C:44]3[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][C:45]=3[N:46]=2)=[CH:38][CH:37]=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>[ClH:51].[ClH:1].[Cl:51][C:48]1[CH:49]=[CH:50][C:44]2[O:43][C:42]([C:39]3[CH:38]=[CH:37][C:36]([CH2:35][O:34][C:28]4[CH:29]=[CH:30][C:31]([F:33])=[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:41][CH:40]=3)=[N:46][C:45]=2[CH:47]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86709819Ethyl 5-{(tert-butoxycarbonyl)[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}-5-fluorophenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

Product 1

HCID 86709817Ethyl 5-{[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}-5-fluorophenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

11 ml of a 4 N solution of hydrogen chloride in dioxane were added to 1025 mg (1.46 mmol) of ethyl 5-{(tert-butoxycarbonyl)[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}-5-fluorophenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate (Enantiomer 2, Example 109A), and the mixture was stirred at room temperature for 2 h. The precipitated solid was filtered off, washed repeatedly with diethyl ether and then dried under high vacuum at 40° C. overnight. This gave 980 mg (1.46 mmol, about 99% of theory) of the target product.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed repeatedly with diethyl ether
  3. customdried under high vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-5b547034ac3a43b6b2a3e20988c097f5
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

Loading…