Methanol → HCID 46836580, compound

HRID 1520200Notes

Reaction equation

HRID 1520200 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[N:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][CH:21]=4)[S:16][C:17]=3[CH3:18])[CH:10]=[N:9]2)=CC=1.C(Cl)Cl.CO>C(O)(C(F)(F)F)=O>[CH3:18][C:17]1[S:16][C:15]([NH:19][C:20]2[N:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][CH:21]=2)=[N:14][C:13]=1[C:11]1[CH:12]=[N:8][NH:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 86658554HCID 86658554, compound

Product 1

HCID 46836580HCID 46836580, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 4 Step 2: A solution of 6-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methylthiazol-2-ylamino)picolinonitrile (0.69 mmol, 277 mg) in TFA (4 mL) was microwaved for 7 minutes at 100° C. After evaporation of the solvent, the resulting residue was neutralized with a saturated solution of Na2CO3. The compound precipitated and after filtration, the solid was washed with water and dried. The solid was finally triturated in Et2O, DCM and MeOH to yield 6-(5-methyl-4-(1H-pyrazol-4-yl)thiazol-2-ylamino)picolinonitrile (90 μmol, 25 mg, 12%) as a beige solid.

Workup

  1. customAfter evaporation of the solvent
  2. customThe compound precipitated
  3. filtrationafter filtration
  4. washthe solid was washed with water
  5. customdried
  6. customThe solid was finally triturated in Et2O

Sources & evidence

ORD record
ord-3e46d4f9915840feb7bc270d138077c7
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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