Hydrochloric Acid → HCID 86603831, compound

HRID 2376193Notes

Reaction equation

HRID 2376193 reaction equation
[O:1]=[C:2]([NH:34][O:35]C1CCCCO1)/[CH:3]=[CH:4]/[C:5]1[CH:6]=[CH:7][C:8]([N:11]([C@@H:19]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[C:30]([CH3:32])([CH3:31])[CH2:29][CH2:28][CH2:27][C:26]=3[CH3:33])[CH2:20]2)C(=O)OC(C)(C)C)=[N:9][CH:10]=1.[ClH:42]>CO>[ClH:42].[ClH:42].[OH:35][NH:34][C:2](=[O:1])/[CH:3]=[CH:4]/[C:5]1[CH:10]=[N:9][C:8]([NH:11][C@@H:19]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[C:30]([CH3:31])([CH3:32])[CH2:29][CH2:28][CH2:27][C:26]=3[CH3:33])[CH2:20]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86603833HCID 86603833, compound

Product 1

HCID 86603831HCID 86603831, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of tert-butyl (5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl}-2-pyridinyl){(3R)-1-[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]-3-pyrrolidinyl}carbamate (80 mg) in methanol (1 mL) was added 4N hydrogen chloride in methanol (3 mL) at ambient temperature and the mixture was stirred at the same temperature for fifteen minutes. The mixture was concentrated in vacuo and the mixture was dissolved in dioxane (1 mL). To this solution was added 4N hydrogen chloride in dioxane (3 mL) and the mixture was stirred at ambient temperature for two hours. The reaction mixture was concentrated in vacuo and the resulting solid was triturated with acetonitrile to give (2E)-N-hydroxy-3-[6-({(3R)-1-[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]-3-pyrrolidinyl}amino)-3-pyridinyl]acrylamide dihydrochloride (40 mg) as a pale tan amorphous solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe mixture was dissolved in dioxane (1 mL)
  3. additionTo this solution was added 4N hydrogen chloride in dioxane (3 mL)
  4. stirringthe mixture was stirred at ambient temperature for two hours
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customthe resulting solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-03ab91a706e2416fb8dad957b8dd7fa6
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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