Hydrochloric Acid → HCID 136335103, compound

HRID 2376184Notes

Reaction equation

HRID 2376184 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([NH:15][C:16]3[N:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[C:24]([NH:26][O:27]C4CCCCO4)=[O:25])=[N:20][CH:21]=3)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:34]>CCO>[ClH:34].[ClH:34].[OH:27][NH:26][C:24](=[O:25])/[CH:23]=[CH:22]/[C:19]1[CH:18]=[N:17][C:16]([NH:15][C@@H:11]2[CH2:12][CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:10]2)=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86603816HCID 86603816, compound

Product 1

HCID 136335103HCID 136335103, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of (2E)-3-(5-{[(3R)-1-(2-phenylethyl)-3-piperidinyl]amino}-2-pyrazinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (3.2 g, 7.1 mmol) in EtOH (16 ml) was added 2M ethanlic hydrogen chloride (17.5 mL) and the mixture was stirred at ambient temperature for 3 hrs. To the reaction mixture was added IPE and isolated precipitate was collected by filtration to give (2E)-N-hydroxy-3-(5-{[(3R)-1-(2-phenylethyl)-3-piperidinyl]amino}-2-pyrazinyl)acrylamide dihydrochloride (2.3 g, 74%) as an amorphous powder.

Workup

  1. additionTo the reaction mixture was added IPE
  2. customisolated precipitate
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-bdccd6b298a74987bf23e1d16aa9dbb7
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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