(6-Methyl-pyridin-2-yl)-thiourea → HCID 46836497, compound

HRID 2366497Notes

Reaction equation

HRID 2366497 reaction equation
Br[CH:2]1[CH2:10][CH2:9][C:8]2[N:7](S(C3C=CC(C)=CC=3)(=O)=O)[N:6]=[CH:5][C:4]=2[C:3]1=O.[CH3:22][C:23]1[N:28]=[C:27]([NH:29][C:30]([NH2:32])=[S:31])[CH:26]=[CH:25][CH:24]=1>CCO.Cl>[CH3:22][C:23]1[N:28]=[C:27]([NH:29][C:30]2[S:31][C:2]3[CH2:10][CH2:9][C:8]4[NH:7][N:6]=[CH:5][C:4]=4[C:3]=3[N:32]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 685983(6-Methyl-pyridin-2-yl)-thioureaHCID 674593295-bromo-1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one

Product 1

HCID 46836497HCID 46836497, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

According to Scheme 3 Step 4: A solution of 5-bromo-1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one (0.90 mmol, 331 mg) and of 1-(6-methylpyridin-2-yl)thiourea (0.90 mmol, 150 mg) in EtOH (10 mL) and HCl (35%, 1 mL) was stirred at 80° C. for 5 hours. The reaction was quenched with the addition of a saturated solution of NaHCO3 at room temperature until pH=8. The aqueous phase was extracted with DCM. The organic phase was dried over Na2SO4 and concentrated. The crude residue was washed with Et2O and dried to yield N-(6-methylpyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine (0.78 mmol, 220 mg, 87%) as a white solid.

Workup

  1. customThe reaction was quenched with the addition of a saturated solution of NaHCO3 at room temperature until pH=8
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. washThe crude residue was washed with Et2O
  6. customdried

Sources & evidence

ORD record
ord-d25b034159644174bbb31df687b8094b
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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