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 1498028Notes

Reaction equation

HRID 1498028 reaction equation
[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

Participants

5

Reactant 2

HCID 43939611,1'-Carbonyl-di-(1,2,4-triazole)3×HCID 178432631HCID 178432631, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4530407b438747139f0193a758ea23e6
Source dataset
uspto-grants-2015_12
Patent number
US09200000B2

Reaction notes

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