Hydrochloric Acid → HCID 67267295, compound

HRID 1465489Notes

Reaction equation

HRID 1465489 reaction equation
[NH:1]([C:10]([O:12][CH2:13][CH2:14][C:15]1[S:16][C:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:34](=[O:36])[CH3:35])[CH2:30][CH2:29]3)=[CH:24][N:23]=2)=[CH:18][CH:19]=1)=[O:11])[NH:2]C(OC(C)(C)C)=O.O1CCOCC1.Cl.Cl>CC(O)C.C(O)C>[NH:1]([C:10]([O:12][CH2:13][CH2:14][C:15]1[S:16][C:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:29][CH2:30][N:31]([C:34](=[O:36])[CH3:35])[CH2:32][CH2:33]3)=[CH:24][N:23]=2)=[CH:18][CH:19]=1)=[O:11])[NH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 204431481,4-Dioxane hydrochlorideHCID 86651848HCID 86651848, compound

Product 1

HCID 67267295HCID 67267295, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 22179027Isopropanol ethanolSolvent

Procedure

By a method similar to Production Example 108, step 8, 2-(5-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}thiophen-2-yl)ethyl tert-butyl hydrazine-1,2-dicarboxylate (corresponding to 0.974 mmol) was treated with 4M hydrogen chloride dioxane solution. The obtained hydrochloride was dissolved in 2-propanol-ethanol (9:1) mixture, and filtered through aminopropylated silica gel. The aminopropylated silica gel was washed with 2-propanol-dichloromethane (1:9), the filtrate and the washing solution were combined and concentrated under reduced pressure to about 20 ml. Hexane (200 ml) was added, and the mixture was concentrated again under reduced pressure to about 40 ml. Hexane (200 ml) was added to the residue and the mixture was stirred. The resulting solid was collected by filtration, washed with hexane and dried under reduced pressure to give the title compound (350.1 mg, yield 86.1%) as a white solid.

Workup

  1. filtrationfiltered through aminopropylated silica gel
  2. washThe aminopropylated silica gel was washed with 2-propanol-dichloromethane (1:9)
  3. concentrationconcentrated under reduced pressure to about 20 ml
  4. additionHexane (200 ml) was added
  5. concentrationthe mixture was concentrated again under reduced pressure to about 40 ml
  6. additionHexane (200 ml) was added to the residue
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with hexane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-49e1a7569f6346b1b166a3c29fcbf200
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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