Aniline → HCID 11438062, compound

HRID 2375023Notes

Reaction equation

HRID 2375023 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:13][C:14]1[N:15]=[C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:17]2[C:22]=1[CH:21]=[N:20][C:19](SC)=[N:18]2.CC1N=C(C2C=CC=CC=2)N2C=1C=NC(S(C)(=O)=O)=N2>O1CCCC1>[CH3:13][C:14]1[N:15]=[C:16]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:17]2[C:22]=1[CH:21]=[N:20][C:19]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N:18]2

Participants

6

Reactant 4

HCID 6115AnilineHCID 534718325-Methyl-2-(methylthio)-7-phenylimidazo[5,1-F][1,2,4]triazineHCID 534718335-Methyl-2-(methylsulfonyl)-7-phenylimidazo[5,1-F][1,2,4]triazineHCID 178418339Butyllithium

Product 1

HCID 11438062HCID 11438062, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of aniline (18 mg, 0.19 mmol) in tetrahydrofuran (5 mL) at −78° C. was treated with n-butyllithium (0.13 mL of a 1.6M solution in hexanes, 0.21 mmol) and the resulting mixture stirred at this temperature for 0.5 h. The mixture was then treated with a solution of of 5-methyl-2-(methylthio)-7-phenylimidazo[5,1-f][1,2,4]triazine (Intermediate 72) (50 mg, 0.17 mmol) in tetrahydrofuran (5 mL) and the mixture allowed to warm slowly to room temperature overnight. The mixture was then reduced under vacuum and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate and the layers separated. The organic layer was then dried with magnesium sulfate, filtered and reduced. The crude product was purified by chromatography on silica gel eluting with 50% ethyl acetate in petrol to afford 5-methyl-N,7-diphenylimidazo[5,1-f][1,2,4]triazin-2-amine (10 mg) as a yellow solid. MS m/z 302 (M+1).

Workup

  1. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. customthe layers separated
  3. dry with materialThe organic layer was then dried with magnesium sulfate
  4. filtrationfiltered
  5. customThe crude product was purified by chromatography on silica gel eluting with 50% ethyl acetate in petrol

Sources & evidence

ORD record
ord-64a20bfc279c49589e9bb7e040e93d6b
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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