HCID 68610342, compound → HCID 178440434, compound

HRID 38228Notes

Reaction equation

HRID 38228 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:17]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:15][N:14]=3)[C:10]([CH2:25][CH2:26][CH3:27])=[N:9]2)=CC=1.COC1C=CC(CN2C(CCC)=C(C3N=C(NC4C=CC=CN=4)SN=3)C=N2)=CC=1>C(O)(C(F)(F)F)=O.ClC(Cl)C>[CH2:25]([C:10]1[C:11]([C:13]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[S:15][N:14]=2)=[CH:12][NH:8][N:9]=1)[CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 68610342HCID 68610342, compoundHCID 68610987HCID 68610987, compound

Product 1

HCID 178440434HCID 178440434, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 1 Step 4: A solution of a mixture of 3-(1-(4-methoxybenzyl)-3-propyl-1H-pyrazol-4-yl)-N-(pyridin-2-yl)-1,2,4-thiadiazol-5-amine and of 3-(1-(4-methoxybenzyl)-5-propyl-1H-pyrazol-4-yl)-N-(pyridin-2-yl)-1,2,4-thiadiazol-5-amine (0.39 mmol, 160 mg) in TFA (2 mL) and dichloroethane (2 mL) was stirred under reflux for 12 hours. After evaporation of the solvent, DCM was added and the organic phase was washed with a saturated solution of NH4OH and brine. Then the organic phase was dried over Na2SO4, was filtered and was concentrated under reduced pressure. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (95:5) as eluent to yield 3-(3-propyl-1H-pyrazol-4-yl)-N-(pyridin-2-yl)-1,2,4-thiadiazol-5-amine (0.24 mmol, 70 mg, 62%) as a white solid.

Workup

  1. temperatureunder reflux for 12 hours
  2. customAfter evaporation of the solvent, DCM
  3. additionwas added
  4. washthe organic phase was washed with a saturated solution of NH4OH and brine
  5. dry with materialThen the organic phase was dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-d36cfde215734d5685294396aa53e9bc
Source dataset
uspto-grants-2013_09
Patent number
US08524718B2

Reaction notes

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