Hydrochloric Acid → HCID 86760791, compound

HRID 2376189Notes

Reaction equation

HRID 2376189 reaction equation
[CH2:1]([CH:3]([CH2:36][CH3:37])[CH2:4][N:5]1[CH2:9][CH2:8][C@@H:7]([N:10]([C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26](=[O:35])[NH:27][O:28]C3CCCCO3)=[CH:20][N:19]=2)C(=O)OC(C)(C)C)[CH2:6]1)[CH3:2].[ClH:38]>CO>[ClH:38].[ClH:38].[CH2:36]([CH:3]([CH2:1][CH3:2])[CH2:4][N:5]1[CH2:9][CH2:8][C@@H:7]([NH:10][C:18]2[N:19]=[CH:20][C:21](/[CH:24]=[CH:25]/[C:26]([NH:27][OH:28])=[O:35])=[CH:22][CH:23]=2)[CH2:6]1)[CH3:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86760793HCID 86760793, compound

Product 1

HCID 86760791HCID 86760791, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of tert-butyl [(3R)-1-(2-ethylbutyl)-3-pyrrolidinyl](5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl}-2-pyridinyl)carbamate (128 mg) in methanol (2.5 mL) was added hydrogen chloride in methanol (0.248 mL). After stirring at room temperature for 1 hour, the reaction mixture was evaporated in vacuo. ii) To a mixture of above product and dioxane (2.5 mL) was added 4N hydrogen chloride in dioxane (1.02 mL). After stirring at room temperature for 2 hours, the reaction mixture was evaporated in vacuo and triturated with ethyl acetate to give (2E)-3-(6-{[(3R)-1-(2-ethylbutyl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-hydroxyacrylamide dihydrochloride (92.0 mg). 1H-NMR (300 MHz, DMSO-d6) δ 0.85 (6H, t, J=7 Hz), 1.28-1.52 (4H, m), 1.58-1.72 (1H, m), 2.02-2.15 (1H, m), 2.32-2.67 (2H, m), 3.06-4.78 (6H, m), 6.37 (1H, d, J=16 Hz), 6.91-7.08 (1H, m), 7.43 (1H, d, J=16 Hz), 7.94-8.02 (1H, m), 8.21 (1H, brs), 10.4 (1H, brs). MS (ES+) m/z 333 (M+1).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionii) To a mixture of above product and dioxane (2.5 mL)
  3. additionwas added 4N hydrogen chloride in dioxane (1.02 mL)
  4. stirringAfter stirring at room temperature for 2 hours
  5. customthe reaction mixture was evaporated in vacuo
  6. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-9084348a37b441e0ad3eb2cada0ae127
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

Loading…