1-(2-Pyridyl)-2-thiourea → HCID 46700737, compound

HRID 2366487Notes

Reaction equation

HRID 2366487 reaction equation
Br[CH:2]1[CH2:10][CH2:9][C:8]2[NH:7][N:6]=[CH:5][C:4]=2[C:3]1=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]([NH2:21])=[S:20].CCOC(C)=O.CO>CC(C)=O>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]1[S:20][C:2]2[CH2:10][CH2:9][C:8]3[NH:7][N:6]=[CH:5][C:4]=3[C:3]=2[N:21]=1

Participants

5

Reactant 3

HCID 14904911-(2-Pyridyl)-2-thioureaHCID 21584119Ethylacetate methanolHCID 59252674HCID 59252674, compound

Product 1

HCID 46700737HCID 46700737, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

According to Scheme 1 Step 4: A solution of 5-bromo-6,7-dihydro-1H-indazol-4(5H)-one (23.3 mmol, 5.00 g) and of 1-(pyridin-2-yl)thiourea (20.9 mmol, 3.21 g) in acetone (60 mL) was stirred at 60° C. for 5 hours. The precipitate formed was filtered and partitioned between AcOEt and a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4 and concentrated to yield a grey solid. The crude residue was purified by flash chromatography over silica gel using DCM/MeOH (95:5) as eluent and by two recristallizations with AcOEt/MeOH (50:50) to yield N-(pyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine (11.9 mmol, 3.20 g, 51%) as a white solid.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. custompartitioned between AcOEt
  4. extractionThe aqueous phase was extracted with AcOEt
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customto yield a grey solid
  8. customThe crude residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-b63eff8775664f649e2748ea235a4d2b
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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