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

HRID 1016419ノート

反応式

HRID 1016419 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

HCID 67485099HCID 67485099、化合物収率 22.8%

試薬・触媒・溶媒 1

HCID 31215Triethyl phosphite溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-1b5af580deac4fb89792f6665a17468b
出典データセット
uspto-grants-2002_11
特許番号
US06476030B1

反応ノート

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