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

HRID 1520225ノート

反応式

HRID 1520225 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-81887a4c0c8d46148b6526d900bc2c10
出典データセット
uspto-grants-2015_07
特許番号
US09073907B2

反応ノート

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