Triethylamine → HCID 136356802, 화합물

HRID 1255195노트

반응식

HRID 1255195 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH:5]=[N:4][CH:3]=1.O.NN.N1C=CN=CC=1[NH:24][NH2:25].C(N(CC)CC)C.C(O[CH:36]=[C:37]([C:43](=O)[C:44]([F:47])([F:46])[F:45])[C:38]([O:40][CH2:41][CH3:42])=[O:39])C>C(O)C.C(#N)C>[OH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[N:7]=[C:2]([N:24]2[C:43]([C:44]([F:47])([F:46])[F:45])=[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:36]=[N:25]2)[CH:3]=[N:4][CH:5]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 14878232-HydrazinopyrazineHCID 4685753Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoateHCID 136284757HCID 136284757, 화합물

생성물 1

HCID 136356802HCID 136356802, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a solution of the title compound from Example 16 Step A (0.500 grams, 2.42 mmol) in ethanol (20 mL) was added hydrazine hydrate (3.25 mL, 35% v/v, 36.3 mmol). The reaction flask was equipped with a reflux condenser, and the reaction mixture was stirred at 80° C. After 12 h, the mixture was allowed to cool to room temperature, whereupon a yellow solid precipitated. The solid was triturated with hexanes, filtered, washed with water, and dried in vacuo: LCMS m/z 203.2 [M+H]+. To a solution of the crude pyrazinyl hydrazine in acetonitrile (10 mL) were added triethylamine (0.675 mL, 4.84 mmol) and ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate (0.872 g, 3.63 mmol). After 40 min at ambient temperature, the reaction mixture was placed in a 60° C. bath and was stirred for 30 min, at which point the reaction mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 60% EtOAc in hexanes, then 60 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 379.1 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 10.98 (s, 1H), 9.35 (s, 1H), 8.85 (s, 1H), 8.23 (s, 1H), 7.93 (dd, J=8.0, 1.5 Hz, 1H), 7.43 (t, J=8.0 Hz, 1H), 7.07 (d, J=8.5 Hz, 1H), 7.04 (t, J=8.0 Hz, 1H).

후처리

  1. customThe reaction flask was equipped with a reflux condenser
  2. temperatureto cool to room temperature, whereupon a yellow solid
  3. customprecipitated
  4. customThe solid was triturated with hexanes
  5. filtrationfiltered
  6. washwashed with water
  7. customdried in vacuo
  8. waitAfter 40 min at ambient temperature
  9. customwas placed in a 60° C.
  10. stirringwas stirred for 30 min, at which
  11. temperatureto cool to ambient temperature
  12. concentrationwas concentrated in vacuo
  13. customPurification by flash chromatography on silica gel (0 to 60% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-ba8f193f0059420bbbb5d568866b5d47
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455638B2

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