Hydrochloride methanol → (2E)-3-(6-{[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-hydroxyacrylamide dihydrochloride

HRID 2376183Notes

Reaction equation

HRID 2376183 reaction equation
[CH:1]1([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([N:12]([C:20]3[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28](=[O:37])[NH:29][O:30]C4CCCCO4)=[CH:22][N:21]=3)C(=O)OC(C)(C)C)[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[ClH:40]>CO>[ClH:40].[ClH:40].[CH:1]1([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][C:20]3[N:21]=[CH:22][C:23](/[CH:26]=[CH:27]/[C:28]([NH:29][OH:30])=[O:37])=[CH:24][CH:25]=3)[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86603680tert-butyl [(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl](5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl)-2-pyridinyl)carbamate

Product 1

HCID 86603812(2E)-3-(6-{[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-hydroxyacrylamide dihydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl](5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl}-2-pyridinyl)carbamate (179 mg, 0.35 mmol) in MeOH (1 mL) was added hydrogen chloride methanol reagent 10 (3 mL, Tokyo Kasei), and the mixture was stirred at ambient temperature for 1 hr. The solvent was removed in vacuo and the residue was dissolved in dioxane (1 mL). To the reaction mixture was added 4N HCl in dioxane (4 mL) and stirred for 1 hr at ambient temperature. To the reaction mixture was added MeCN and the solvent was removed in vacuo. Obtained colorless solid was triturated with MeCN to give (2E)-3-(6-{[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-hydroxyacrylamide dihydrochloride (115 mg, 85%) as colorless powder.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dioxane (1 mL)
  3. additionTo the reaction mixture was added 4N HCl in dioxane (4 mL)
  4. stirringstirred for 1 hr at ambient temperature
  5. additionTo the reaction mixture was added MeCN
  6. customthe solvent was removed in vacuo
  7. customObtained colorless solid
  8. customwas triturated with MeCN

Sources & evidence

ORD record
ord-8c169d16712247748055c0482e3b2528
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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