p-Toluenesulfonic acid → 5-methyl-N-[4-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375022

반응식

HRID 2375022 반응식
[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7](SC)=[N:6]2.CC1N=C(C2C=CC=CC=2)N2C=1C=NC(S(C)(=O)=O)=N2.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:47][C:44]1[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][CH:43]=1)=[N:6]2

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 7732P-AnisidineHCID 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]triazine

생성물 1

HCID 445897295-methyl-N-[4-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine수율 23.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 5-methyl-2-(methylthio)-7-phenylimidazo[5,1-f][1,2,4]triazine (Intermediate 72) (75 mg, 0.26 mmol), p-anisidine (32 mg, 0.26 mmol) and p-toluenesulfonic acid (5 mg, 0.03 mmol) in tetrahydrofuran (5 mL) was stirred at reflux overnight. The mixture was then reduced under vacuum, and purified by chromatography on silica gel eluting with 40% ethyl acetate in petrol to give a solid which was purified further by trituration with diethyl ether to afford 5-methyl-N-[4-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine (20 mg) as a yellow solid. MS m/z 332 (M+1).

후처리

  1. temperatureat reflux overnight
  2. custompurified by chromatography on silica gel eluting with 40% ethyl acetate in petrol
  3. customto give a solid which
  4. customwas purified further by trituration with diethyl ether

출처 및 근거

ORD 기록
ord-88e2f0a548fc4ef6a869887740058b12
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462614B2

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