Hydrochloric Acid → HCID 86684814, compound

HRID 1527982Notes

Reaction equation

HRID 1527982 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9](=[O:38])[CH2:10][C@H:11]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[N:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9](=[O:38])[CH2:10][C@H:11]([C:19]1[CH:20]=[CH:21][C:22]([CH:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]2)=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86684815HCID 86684815, compound

Product 1

HCID 86684814HCID 86684814, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-tert-butyl 4-(4-(3-(3-methoxypyridazin-4-yl)-3-oxo-1-o-tolylpropyl)-phenyl)piperidine-1-carboxylate (118 mg, 195 μmol) in 1,4-dioxane (4 mL) was added 37% aq. hydrochloric acid solution (0.32 mL, 3.9 mmol), then after 30 min the reaction mixture was partitioned between ethyl acetate and sat, aq. sodium hydrogencarbonte-solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; gradient dichloromethane to dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) afforded the title compound (64 mg, 79%). Orange gum, MS: 416.2 [M+H]+.

Workup

  1. customafter 30 min the reaction mixture was partitioned between ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-220b760f32d24bfd87ebf67b667af44d
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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