Diisopropyl Ether → 2-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-1,3-benzoxazole-5-carboxylic acid hydrochloride

HRID 1691743Notes

Reaction equation

HRID 1691743 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[O:29][C:30]3[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][C:31]=3[N:32]=2)[CH2:24][CH:23]1[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[ClH:47].C(OCC)(=O)C.C(OC(C)C)(C)C>O1CCOCC1>[ClH:47].[F:46][C:42]1[CH:41]=[C:40]([CH:23]2[CH:22]([CH2:21][NH:8][C@@H:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH2:27][CH2:26][N:25]([C:28]3[O:29][C:30]4[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][C:31]=4[N:32]=3)[CH2:24]2)[CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 669060422-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-1,3-benzoxazole-5-carboxylic acid

Product 1

HCID 669059512-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-1,3-benzoxazole-5-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 35 mg of 2-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-1,3-benzoxazole-5-carboxylic acid in 1.0 mL of 1,4-dioxane solution was added 1.00 mL of a 4 M hydrogen chloride/ethyl acetate solution at room temperature, followed by stirring for 1 hour. Diisopropyl ether was added thereto, and the resulting precipitate was collected by filtration, and dried under reduced pressure to obtain 14 mg of 2-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-1,3-benzoxazole-5-carboxylic acid hydrochloride.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-64d4f796c7414e9e9b0d16deb634705c
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

Loading…