Water → HCID 46836733, compound

HRID 1520198Notes

Reaction equation

HRID 1520198 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][N:21]=4)[S:16][C:17]=3[CH3:18])[CH:10]=[N:9]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+].O>C(O)(C(F)(F)F)=O>[F:26][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([NH:19][C:15]2[S:16][C:17]([CH3:18])=[C:13]([C:11]3[CH:12]=[N:8][NH:9][CH:10]=3)[N:14]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 86658552HCID 86658552, compound

Product 1

HCID 46836733HCID 46836733, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 3 Step 3: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methylthiazol-2-yl)-4-fluoropyridin-2-amine (0.33 mmol, 132 mg) in TFA (1.5 mL) was microwaved for 2 minutes at 150° C. A precipitate was formed after addition of a saturated solution of Na2CO3 and water. After filtration, the solid was washed with water and recrystallized in Et2O to yield N-(4-fluoropyridin-2-yl)-5-methyl-4-(1H-pyrazol-4-yl)thiazol-2-amine (0.17 mmol, 47 mg, 51%) as a beige solid.

Workup

  1. customA precipitate was formed
  2. filtrationAfter filtration
  3. washthe solid was washed with water
  4. customrecrystallized in Et2O

Sources & evidence

ORD record
ord-4f23b1a574024e8fa747b1c5eb60b31e
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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