1,4-Dioxane hydrochloride → HCID 66906234, compound

HRID 1691689Notes

Reaction equation

HRID 1691689 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)[CH2:26][CH2:25][N:24]([C:35]([NH:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=2)=[O:36])[CH2:23]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].O1CCOCC1>>[ClH:47].[F:34][C:30]1[CH:29]=[C:28]([CH:27]2[CH2:26][CH2:25][N:24]([C:35]([NH:37][C:38]3[CH:39]=[CH:40][C:41]([C:42]([OH:44])=[O:43])=[CH:45][CH:46]=3)=[O:36])[CH2:23][CH:22]2[CH2:21][NH:8][C@@H:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66906192HCID 66906192, compound

Product 1

HCID 66906234HCID 66906234, compound

Procedure

To 354 mg of 4-({[3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-(3-fluorophenyl)piperidin-1-yl]carbonyl}amino)benzoic acid was added 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added isopropanol, followed by heating for dissolution. Diisopropylether was added dropwise thereto, and the precipitate was isolated by filtration, and dried under reduced pressure to obtain 180 mg of 4-({[4-(3-fluorophenyl)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]carbonyl}amino)benzoic acid hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added isopropanol
  3. temperatureby heating for dissolution
  4. additionDiisopropylether was added dropwise
  5. customthe precipitate was isolated by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-fa46d6bd3c6e4c9bac09be9f3677658b
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

Loading…