Hydrochloric Acid → 1-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine

HRID 62522노트

반응식

HRID 62522 반응식
[CH2:1]([O:3][CH2:4][C:5](=O)[CH2:6][C:7]#[N:8])[CH3:2].C(O)(=O)C(O)=O.[CH2:16]([NH:18][NH2:19])[CH3:17].Cl>C(O)C>[CH2:16]([N:18]1[C:7]([NH2:8])=[CH:6][C:5]([CH2:4][O:3][CH2:1][CH3:2])=[N:19]1)[CH3:17]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 575169104-Ethoxy-3-oxobutanenitrile

생성물 1

HCID 575169111-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine수율 51.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a 25 mL round bottom was added 4-(ethyloxy)-3-oxobutanenitrile (550 mg, 4.33 mmol), ethyl hydrazine oxalate (641 mg, 4.33 mmol), and HCl (2.163 mL, 4.33 mmol) in ethanol (10 mL). The reaction mixture was stirred at the room temperature overnight. The reaction mixture was then evaporated, and partitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3. The organic layer was washed with brine, filtered and evaporated. 1-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine (420 mg, 2.234 mmol, 51.6% yield) was isolated as yellow oil. The product was used in the next step without further purification. LCMS (M+H)+=170.1 (M+H); 1H NMR (400 MHz, DMSO-d6) ppm 1.08 (t, J=6.95 Hz, 3 H) 1.19 (t, J=7.07 Hz, 3 H) 3.37-3.43 (m, 2 H) 3.81 (q, J=7.24 Hz, 2 H) 4.15 (s, 2 H) 5.09 (s, 2 H) 5.22 (s, 1 H).

후처리

  1. customThe reaction mixture was then evaporated
  2. custompartitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3
  3. washThe organic layer was washed with brine
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-7385e4c7750341ceadf0ce305a7bca18
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446034B2

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