[1,2,4]Triazolo[1,5-a]pyrazine-2-carboxylic acid, ethyl ester, 3-oxide → HCID 67485099, 화합물

HRID 1016419노트

반응식

HRID 1016419 반응식
[N:1]1[C:2]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N+:3]([O-])[N:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=12>P(OCC)(OCC)OCC>[CH2:14]([O:13][C:11]([C:2]1[N:1]=[C:5]2[CH:6]=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1)=[O:12])[CH3:15]

참가 물질

3

반응물 1

HCID 12308357[1,2,4]Triazolo[1,5-a]pyrazine-2-carboxylic acid, ethyl ester, 3-oxide

생성물 1

HCID 67485099HCID 67485099, 화합물수율 22.8%

시약·촉매·용매 1

HCID 31215Triethyl phosphite용매

실험 절차

Ethyl 1,2,4-triazolo[1,5-a]pyrazine-2-carboxylate-3-oxide (prepared as described in J. Chem. Soc., Perkin Trans. 1, 1976, 2166) (2.0 g, 9.6 mmol) was stirred in triethyl phosphite (20 ml) at 100° C. for 1 h. The solvent was concentrated in vacuo, and the crude product was triturated with diethyl ether (50 ml). The precipitated solid was separated by filtration, and purified by flash chromatography on silica gel, eluting with 1:1 dichloromethane:ethyl acetate, yielding [1,2,4]triazolo[1,5-a]pyrazine-2-carboxylic acid ethyl ester as a pale orange solid (420 mg). Data for the title compound: 1H NMR (360 MHz, CDCl3) δ 1.51 (3H, t, J=7.1 Hz), 4.59 (2H, q, J=7.1 Hz), 8.34 (1H, d, J=4.5 Hz), 8.63 (1H, d, J=4.5 Hz), 9.43 (1H, s); MS (ES+) m/e 193 [MH]+.

후처리

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe crude product was triturated with diethyl ether (50 ml)
  3. customThe precipitated solid was separated by filtration
  4. custompurified by flash chromatography on silica gel
  5. washeluting with 1:1 dichloromethane

출처 및 근거

ORD 기록
ord-1b5af580deac4fb89792f6665a17468b
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476030B1

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