Hydrochloric Acid → HCID 178445667, compound

HRID 2368162Notes

Reaction equation

HRID 2368162 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH:23]([OH:25])[CH3:24])[CH2:17][CH2:16]2)[CH:10]=3)[CH2:3][CH2:2]1.[CH2:26](N(CC)CC)C.[S:33](Cl)(Cl)(=[O:35])=[O:34].Cl>C1COCC1>[CH3:26][S:33]([O:25][CH:23]([CH3:24])[CH2:22][CH2:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([N:11]2[CH:10]=[C:9]3[C:13]([CH:14]=[C:6]([O:5][CH2:4][CH:1]4[CH2:3][CH2:2]4)[CH:7]=[CH:8]3)=[N:12]2)[CH2:16][CH2:17]1)(=[O:35])=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 178467818HCID 178467818, compound

Product 1

HCID 178445667HCID 178445667, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-{trans-4-[6-(cyclopropylmethoxy)-2H-indazol-2-yl]cyclohexyl}butan-2-ol (2.45 g) and triethylamine (1.50 mL) in THF (50 mL) was added dropwise a solution of sulfonyl chloride (0.83 mL) in THF (50 mL) under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling. The reaction mixture was poured into 1N hydrochloric acid under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (2.98 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water, aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-956a34cd5f4b4650979d028ff3fc8114
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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