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

HRID 2177660노트

반응식

HRID 2177660 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7e0cd36d285a40499e28f96f2f7394c8
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067920B2

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