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4-Bromobenzenesulfonamide → 4-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]benzenesulfonamide

HRID 2374898
Notes
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Reaction equation

HRID 2374898 reaction equation
Cl.[CH3:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH2:12])=[N:7]2.Br[C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:2][C:3]1[N:4]=[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH:12][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 696964-BromobenzenesulfonamideHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 688705435-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride

Product 1

HCID 112111914-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]benzenesulfonamideYield 3.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a mixture of 5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride (0.026 g, 0.10 mmol), 4-bromobenzenesulfonamide (0.026 g, 0.11 mmol), tris(dibenzylideneacetone)dipalladium (2.7 mg, 0.0030 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (5.6 mg, 0.0090 mmol) and sodium t-butoxide (0.025 g, 0.23 mmol) was added dioxane (1 mL). The solution was heated with microwave radiation to 160° C. for 15 minutes. After cooling to room temperature, the solution was filtered, and silica gel (1 g) was added, followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to a gradient elution using ethyl acetate:hexanes (50:50) to ethyl acetate:hexanes (100:0) using a RediSep silica gel cartridge (4 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give 4-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]benzenesulfonamide (0.0015 g) as a yellow solid. MS m/z 381 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solution was filtered
  3. additionsilica gel (1 g) was added
  4. customfollowed by evaporation of the volatiles under reduced pressure
  5. washsubjected to a gradient elution
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdf9d2b8aa514439b0aab67446757cb1
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07462614B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes