Acetic Acid → 4-(5-fluoro-2-(6-methylpyridin-2-ylamino)thiazol-4-yl)-1H-pyrazole-1-carboxamide

HRID 1520225Notes

Reaction equation

HRID 1520225 reaction equation
[F:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)=[N:4][C:3]=1[C:15]1[CH:16]=[N:17][NH:18][CH:19]=1.[O-:20][C:21]#[N:22].[K+].CC(O)=O>O>[F:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)=[N:4][C:3]=1[C:15]1[CH:16]=[N:17][N:18]([C:21]([NH2:22])=[O:20])[CH:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 468367265-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine

Product 1

HCID 468368694-(5-fluoro-2-(6-methylpyridin-2-ylamino)thiazol-4-yl)-1H-pyrazole-1-carboxamideYield 3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to Scheme 19: A solution of N-(5-fluoro-4-(1H-pyrazol-4-yl)thiazol-2-yl)-6-methylpyridin-2-amine (1.22 mmol, 337 mg), potassium cyanate (1.47 mmol, 119 mg), AcOH (5 mL) and water (5 mL) was stirred for 2.5 hours at room temperature. The reaction mixture was quenched with water (100 mL) and the precipitate was filtered. The resulting crude product was purified by flash chromatography over silica gel using DCM/EDA (80:20; EDA: DCM/EtOH/NH3 90:9:1) as eluent to yield 4-(5-fluoro-2-(6-methylpyridin-2-ylamino)thiazol-4-yl)-1H-pyrazole-1-carboxamide (31 μmol, 10 mg, 3%) as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. filtrationthe precipitate was filtered
  3. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-81887a4c0c8d46148b6526d900bc2c10
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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