Hydrochloride methanol → HCID 86603790, compound

HRID 2376173Notes

Reaction equation

HRID 2376173 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([N:11]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27](=[O:36])[NH:28][O:29]C3CCCCO3)=[CH:21][N:20]=2)C(=O)OC(C)(C)C)[CH2:7]1.CO.[ClH:42]>CO>[ClH:42].[ClH:42].[F:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:19]2[N:20]=[CH:21][C:22](/[CH:25]=[CH:26]/[C:27]([NH:28][OH:29])=[O:36])=[CH:23][CH:24]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86603656HCID 86603656, compound

Product 1

HCID 86603790HCID 86603790, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [(3R)-1-(3-fluorobenzyl)-3-pyrrolidinyl](5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl}-2-pyridyl)carbamate [(251 g) in MeOH (37 mL) was added hydrogen chloride methanol reagent 10 (9.28 mL, Tokyo Kasei), and the mixture was stirred at ambient temperature for 1 hour. The solvent was removed in vacuo and the residue was dissolved in dioxane (12 mL). To the reaction mixture was added 4N HCl in dioxane and stirred for 1 hour at ambient temperature. To the reaction mixture was added CH3CN and the solvent was removed in vacuo. Obtained colorless solid was triturated with CH3CN to give (2E)-3-(6-{[(3R)-1-(3-fluorobenzyl)-3-pyrrolidinyl]amino}-3-pyridyl)-N-hydroxyacrylamide dihydrochloride (1.87 g) as colorless powder.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dioxane (12 mL)
  3. additionTo the reaction mixture was added 4N HCl in dioxane
  4. stirringstirred for 1 hour at ambient temperature
  5. additionTo the reaction mixture was added CH3CN
  6. customthe solvent was removed in vacuo
  7. customObtained colorless solid
  8. customwas triturated with CH3CN

Sources & evidence

ORD record
ord-afa8962115f44368968608c8dbd444e7
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

Loading…