Acetic Acid → 5-(2-Methoxy-6-methyl-pyridin-3-yl)-2H-pyrazol-3-ylamine

HRID 2177660ノート

反応式

HRID 2177660 の反応式
CO[C:3]1[C:8]([C:9](=O)[CH2:10][C:11]#[N:12])=[CH:7][CH:6]=[C:5]([CH3:14])[N:4]=1.[OH2:15].[NH2:16][NH2:17].[C:18](O)(=O)C>C(O)C>[CH3:18][O:15][C:3]1[C:8]([C:9]2[CH:10]=[C:11]([NH2:12])[NH:16][N:17]=2)=[CH:7][CH:6]=[C:5]([CH3:14])[N:4]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 690956553-(2-Methoxy-6-methyl-pyridin-3-yl)-3-oxo-propionitrile

生成物 1

HCID 1784941675-(2-Methoxy-6-methyl-pyridin-3-yl)-2H-pyrazol-3-ylamine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

A solution of 3-(2-methoxy-6-methyl-pyridin-3-yl)-3-oxo-propionitrile (21 g, 110.4 mmol) in ethanol (200 mL) is placed in a sealed tube, Hydrazine, hydrate (32.1 mL, 662.4 mmol) and acetic acid (21.0 mL) are added and the reaction heated at 100° C. for 2 h. The solvent is evaporated off and the reaction mixture is diluted with EtOAc (500 mL) and saturated sodium bicarbonate solution (100 mL). The organic layer is separated and the aqueous layer is extracted with EtOAc (2×250 mL). The combined organic extracts are dried over Na2SO4, filtered, and concentrated to give the crude product which is taken into the next step without any further purification. Yield=16.5 g (73%). 1H NMR (400 MHz, DMSO-d6) δ 11.50 (bs, 1H), 7.90 (d, J=7.6 Hz, 1H), 6.86 (d, J=7.6 Hz, 1H), 5.88 (s, 1H), 4.64 (s, 3H), 2.38 (s, 3H).

後処理

  1. customThe solvent is evaporated off
  2. additionthe reaction mixture is diluted with EtOAc (500 mL) and saturated sodium bicarbonate solution (100 mL)
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with EtOAc (2×250 mL)
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-7e0cd36d285a40499e28f96f2f7394c8
出典データセット
uspto-grants-2015_06
特許番号
US09067920B2

反応ノート

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