Hydrochloride methanol → HCID 86603778, compound

HRID 226471Notes

Reaction equation

HRID 226471 reaction equation
[C:1]1([CH:7]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:8]2[CH2:12][CH2:11][C@@H:10]([N:13]([C:21]3[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[C:29](=[O:38])[NH:30][O:31]C4CCCCO4)=[CH:23][N:22]=3)C(=O)OC(C)(C)C)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[ClH:47]>CO>[ClH:47].[ClH:47].[C:39]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:12][CH2:11][C@@H:10]([NH:13][C:21]3[N:22]=[CH:23][C:24](/[CH:27]=[CH:28]/[C:29]([NH:30][OH:31])=[O:38])=[CH:25][CH:26]=3)[CH2:9]2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86603637HCID 86603637, compound

Product 1

HCID 86603778HCID 86603778, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl [(3R)-1-(diphenylmethyl)-3-pyrrolidinyl](5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl}-2-pyridyl)carbamate (94 mg) in methanol (2 mL) was added hydrogen chloride methanol reagent 10 (0.5 mL, Tokyo Kasei), and the mixture was stirred at ambient temperature for 30 minutes. The solvent was evaporated to dryness and the residue was dissolved in the mixture of dioxane (3 ml) and methanol (1 ml). To this solution was added 4N-hydrogen chloride in dioxane (3 ml) and the mixture was stirred at ambient temperature for 3 hours. The solvent was evaporated to dryness and the residue was triturated with acetonitrile to give (2E)-3-(6-{[(3R)-1-(diphenylmethyl)-3-pyrrolidinyl]amino}-3-pyridyl)-N-hydroxyacrylamide dihydrochloride (63 mg) as a pale yellow powder.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue was dissolved in the mixture of dioxane (3 ml) and methanol (1 ml)
  3. additionTo this solution was added 4N-hydrogen chloride in dioxane (3 ml)
  4. stirringthe mixture was stirred at ambient temperature for 3 hours
  5. customThe solvent was evaporated to dryness
  6. customthe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-da0f18822afa4b2c9723030cacffba95
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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