Hydrochloric Acid → HCID 86684817, compound

HRID 1527984Notes

Reaction equation

HRID 1527984 reaction equation
C[O:2][C:3]1[N:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9](=[O:35])[CH2:10][C@H:11]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[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>[CH3:34][S:31]([N:28]1[CH2:27][CH2:26][CH:25]([C:22]2[CH:23]=[CH:24][C:19]([C@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH2:10][C:9]([C:8]3[C:3](=[O:2])[NH:4][N:5]=[CH:6][CH:7]=3)=[O:35])=[CH:20][CH:21]=2)[CH2:30][CH2:29]1)(=[O:33])=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86684816HCID 86684816, compound

Product 1

HCID 86684817HCID 86684817, compoundYield 112.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-1-(3-methoxypyridazin-4-yl)-3-(4-(1-(methylsulfonyl)piperidin-4-yl)phenyl)-3-o-tolylpropan-1-one (example 12, step 4; 50 mg, 0.10 mmol) in 1,4-dioxane (1.5 mL) was added 37% aq. hydrochloric acid solution (0.17 mL, 2.0 mmol) and the resulting solution was heated at 80° C. for 2½ h, then after cooling partitioned between ethyl acetate and sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to produce the title compound (54 mg), which was directly used in the next step. Colorless gum, MS: 480.3 [M+H]+.

Workup

  1. temperatureafter cooling
  2. custompartitioned between ethyl acetate and sat. aq. sodium hydrogencarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-98d3605968e040e1b7b16424cfcc2097
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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