1,1'-Carbonyl-di-(1,2,4-triazole) → 5-(5-bromo-1-methyl-1H-pyrazol-4-yl)-7-methylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

HRID 1907196ノート

反応式

HRID 1907196 の反応式
[C:1](N1C=NC=N1)(N1C=NC=N1)=[O:2].[Br:13][C:14]1[N:18]([CH3:19])[N:17]=[CH:16][C:15]=1[C:20]1[N:21]=[C:22]([CH3:28])[N:23]([NH:25][CH:26]=[NH:27])[CH:24]=1>O1CCOCC1.CO>[Br:13][C:14]1[N:18]([CH3:19])[N:17]=[CH:16][C:15]=1[C:20]1[N:21]=[C:22]([CH3:28])[N:23]2[C:24]=1[C:1](=[O:2])[NH:27][CH:26]=[N:25]2

参加物

5

反応物 2

HCID 43939611,1'-Carbonyl-di-(1,2,4-triazole)3 回HCID 178432631HCID 178432631、化合物

生成物 1

HCID 1363502835-(5-bromo-1-methyl-1H-pyrazol-4-yl)-7-methylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

1,1′-Carbonylbis(1H-1,2,4-triazole) (90%, 2.69 g, 14.8 mmol) and N-[4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-yl]imidoformamide (2.69 g, 9.50 mmol) were combined in 1,4-dioxane (63 mL) and the mixture was stirred for 3.5 hours at room temperature, then heated to 50° C. for 1 hour. Additional 1,1′-carbonylbis(1H-1,2,4-triazole) (90%, 1.34 g, 7.35 mmol) was added, and heating was continued for 30 minutes. After another addition of 1,1′-carbonylbis(1H-1,2,4-triazole) (90%, 269 mg, 1.48 mmol), heating at 50° C. was carried out for an additional 75 minutes. The reaction was allowed to cool to room temperature, and was then concentrated to half its original volume; the precipitate was collected and washed with ethyl acetate to afford a white solid. This was dissolved in methanol (50 mL), concentrated to dryness and triturated with water (25 mL). After collection of the solid, it was washed with 2-propanol followed by diethyl ether to provide C3 as a white solid. Yield: 1.95 g, 6.31 mmol, 66%. LCMS m/z 309.4 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 2.53 (s, 3H), 3.87 (s, 3H), 7.87 (s, 1H), 8.17 (s, 1H), 11.69 (br s, 1H).

後処理

  1. temperatureheated to 50° C. for 1 hour
  2. temperatureheating
  3. waitwas continued for 30 minutes
  4. temperatureheating at 50° C.
  5. waitwas carried out for an additional 75 minutes
  6. temperatureto cool to room temperature
  7. concentrationwas then concentrated to half its original volume
  8. customthe precipitate was collected
  9. washwashed with ethyl acetate
  10. customto afford a white solid
  11. concentrationconcentrated to dryness
  12. customtriturated with water (25 mL)
  13. customAfter collection of the solid, it
  14. washwas washed with 2-propanol

出典と根拠

ORDレコード
ord-fa46db6c5a584c559dd59247e3892269
出典データセット
uspto-grants-2013_12
特許番号
US08598155B2

反応ノート

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