Hydrochloric Acid → HCID 178509557, compound

HRID 1624034Notes

Reaction equation

HRID 1624034 reaction equation
O[C:2]1([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[CH2:10][CH2:9][CH2:8][C:7]2[N:6](S(C3C=CC(C)=CC=3)(=O)=O)[N:5]=[CH:4][C:3]1=2.OC1(C2C=CC(C#N)=CC=2)CCCC2C1=CN(S(C1C=CC(C)=CC=1)(=O)=O)N=2.Cl.O1CCOCC1>>[N:6]1[NH:5][CH:4]=[C:3]2[C:7]=1[CH2:8][CH2:9][CH:10]=[C:2]2[C:21]1[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71114822HCID 71114822, compoundHCID 71114833HCID 71114833, compound

Product 1

HCID 178509557HCID 178509557, compoundYield 67%

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[4-hydroxy-1-(p-tolylsulfonyl)-6,7-dihydro-5H-indazol-4-yl]benzonitrile and 4-[4-hydroxy-2-(p-tolylsulfonyl)-6,7-dihydro-5H-indazol-4-yl]benzonitrile (8.56 g, 21.7 mmol) is added to 4.0 M HCl in dioxane (20.0 mL, 80.0 mmol), heated to 80° C. for 2.0 h and concentrated to dryness. The residue is dissolved in dichloromethane/water, separated and the organics are dried over Na2SO4, filtered, and evaporated. The residue is purified by silica gel chromatography 80% ethyl acetate/hexanes to give the title compound (3.21 g, 67%). ES/MS m/z 222 (M+H), 220 (M−H).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue is dissolved in dichloromethane/water
  3. customseparated
  4. dry with materialthe organics are dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by silica gel chromatography 80% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4a549060d5be4e608fd3eb69e7f84071
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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