Hydrochloric Acid → HCID 23138514, compound

HRID 1171671Notes

Reaction equation

HRID 1171671 reaction equation
[ClH:1].Cl.C([S:6][CH:7]1[CH2:12][CH2:11][N:10]([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH2:9]/[C:8]/1=[CH:26]\[C:27]1[N:31]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[N:30]=[N:29][CH:28]=1)(=O)C.[CH2:38](O)C>>[ClH:1].[CH:16]1([C:14](=[O:15])[CH:13]([N:10]2[CH2:11][CH2:12][CH:7]([SH:6])/[C:8](=[CH:26]/[C:27]3[N:31]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:30]=[N:29][CH:28]=3)/[CH2:9]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86609425HCID 86609425, compound

Product 1

HCID 23138514HCID 23138514, compoundYield 68%

Conditions

Temperature
0 °C

Procedure

Hydrogen chloride was passed through a solution of (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-({1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-5-yl}methylidene)piperidine hydrochloride (2.0 g) in ethanol (5.0 ml) with stirring at 0° C. for one hour, and the resulting mixture was stirred at room temperature under tightly sealed condition for 4 hours. After the reaction mixture was concentrated under reduced pressure, the residue was purified using preparative HPLC [YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024 N aqueous hydrochloric acid solution (33:67, v/v)]. The eluate was treated with hydrogen chloride (4 N dioxane solution, 2 ml). The solvent and excess hydrogen chloride were removed under reduced pressure to afford the title compound (1.29 g, yield: 68%) as a colourless amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature under tightly sealed condition for 4 hours
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified
  4. additionThe eluate was treated with hydrogen chloride (4 N dioxane solution, 2 ml)
  5. customThe solvent and excess hydrogen chloride were removed under reduced pressure

Sources & evidence

ORD record
ord-b4dcd14bd8e84541a94ebecffe9ff6dc
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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