Sodium Hydroxide → HCID 136030806, compound

HRID 1910850Notes

Reaction equation

HRID 1910850 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[S:17][N:16]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[N:14]=3)[CH:10]=[N:9]2)=CC=1.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[NH:9]1[CH:10]=[C:11]([C:13]2[S:17][N:16]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:14]=2)[CH:12]=[N:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67344552HCID 67344552, compound

Product 1

HCID 136030806HCID 136030806, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 2 Step 4: A solution of N-(5-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1,2,4-thiadiazol-3-yl)pyridin-2-amine (69 mmol, 25 mg) in TFA (686 μL) was microwaved for 5 minutes at 120° C. The reaction mixture was neutralized with a solution of NaOH (1 M) and was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM/EtOH/NH3 (100:0:0 to 90:9:1) as eluent to yield 5-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)-1,2,4-thiadiazol-3-amine (13 mmol, 3.3 mg, 19%) as a yellow solid.

Workup

  1. extractionwas extracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated
  5. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-e6e0ad56e73a4f4eaadc89abfcdfe50f
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

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