1-(2-Pyridyl)-2-thiourea → HCID 178434162, compound

HRID 2366501Notes

Reaction equation

HRID 2366501 reaction equation
Br[C:2]1(Br)[CH2:10][CH2:9][C:8]2[NH:7][N:6]=[C:5]([CH3:11])[C:4]=2[C:3]1=O.BrC1CCC2NN=C(C)C=2C1=O.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33]([NH2:35])=[S:34]>CCO>[CH3:11][C:5]1[C:4]2[C:3]3[N:35]=[C:33]([NH:32][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=4)[S:34][C:2]=3[CH2:10][CH2:9][C:8]=2[NH:7][N:6]=1

Participants

5

Reactant 3

HCID 14904911-(2-Pyridyl)-2-thioureaHCID 178434188HCID 178434188, compoundHCID 178434189HCID 178434189, compound

Product 1

HCID 178434162HCID 178434162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to Scheme 4 Step 5: A solution of a mixture of 5,5-dibromo-3-methyl-6,7-dihydro-1H-indazol-4(5H)one, 5-bromo-3-methyl-6,7-dihydro-1H-indazol-4(5H)-one (37.5:62.5, 173 mg) and of 1-(pyridin-2-yl)thiourea (0.67 mmol, 102 mg) in EtOH (2.4 mL) was stirred under reflux for 3 hours. The precipitate formed was filtered, was washed with a saturated solution of NaHCO3, water, EtOH and Et2O and was dried to yield 8-methyl-N-(pyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine (46 μmol, 13 mg) as a white solid.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwas washed with a saturated solution of NaHCO3, water, EtOH and Et2O
  5. customwas dried

Sources & evidence

ORD record
ord-66422ee754a649098cde112db6d8d9b7
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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