Hydrochloric Acid → (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoro-N-hydroxyacrylamide dihydrochloride

HRID 226487Notes

Reaction equation

HRID 226487 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:4]=[C:5](/[CH:23]=[C:24](\[F:35])/[C:25]([NH:27][O:28]C2CCCCO2)=[O:26])[CH:6]=[N:7][C:8]=1[NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:11]1.CCOC(C)=O>CCO>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:4]=[C:5](/[CH:23]=[C:24](\[F:35])/[C:25]([NH:27][OH:28])=[O:26])[CH:6]=[N:7][C:8]=1[NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86603698(2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoro-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide

Product 1

HCID 86603820(2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoro-N-hydroxyacrylamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M ethanolic hydrogen chloride (2.0 mL) was added to the solution of (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoro-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (0.5 g) in EtOH (5 ml) and the mixture was stirred at ambient temperature for 3 hrs. To the reaction mixture was added AcOEt and isolated precipitate was collected by filtration to give (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoro-N-hydroxyacrylamide dihydrochloride (0.28 g),

Workup

  1. customisolated precipitate
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e206d9ba4c99412f9416be91447ab553
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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