6-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine → 7-Cyclobutyl-6-(5,6-dihydro-8H-1,2,4-triazolo[1,5-alpha]pyrazin-7-yl)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

HRID 277333

反応式

HRID 277333 の反応式
Cl[C:2]1[C:3]([CH:17]2[CH2:20][CH2:19][CH2:18]2)=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.[N:21]1[CH:22]=[N:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][C:25]=12>CS(C)=O>[CH:17]1([C:3]2[C:2]([N:27]3[CH2:28][CH2:29][N:24]4[N:23]=[CH:22][N:21]=[C:25]4[CH2:26]3)=[N:7][N:6]3[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][N:10]=[C:5]3[CH:4]=2)[CH2:20][CH2:19][CH2:18]1

参加物

4

反応物 2

HCID 110005936-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazineHCID 184069195H,6H,7H,8H-(1,2,4)triazolo(1,5-a)pyrazine

生成物 1

HCID 541615477-Cyclobutyl-6-(5,6-dihydro-8H-1,2,4-triazolo[1,5-alpha]pyrazin-7-yl)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine収率 26.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 6-chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (150 mg, 0.53 mmol) and 5,6,7,8-tetrahydro-1,2,4-triazolo[1,5-α]pyrazine (190 mg, 1.53 mmol) in dimethyl sulphoxide (1 ml) was stirred and heated at 150° C. for 20 hours. The mixture was partitioned between dichloromethane and water. The aqueous phase was further extracted with dichloromethane (x2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 3→4% methanol-dichloromethane to give the title compound (52 mg, 26%) as an off-white solid (after trituration with diethyl ether). 1H NMR (360 MHz, CDCl3) δ 2.00-2.28 (4H, m), 2.48-2.55 (2H, m), 3.68-3.80 (3H, m), 4.43 (2H, t, J=5.5 Hz), 4.67 (2H, s), 7.46-7.56 (3H, m), 7.97 (1H, s), 8.09 (1H, s),8.37 (2H, br d, J=8 Hz); MS (ES+) m/e 373 [MH]+.

後処理

  1. customThe mixture was partitioned between dichloromethane and water
  2. extractionThe aqueous phase was further extracted with dichloromethane (x2)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with 3→4% methanol-dichloromethane

出典と根拠

ORDレコード
ord-983a399c0c574c15a5e782ea01d8e685
出典データセット
uspto-grants-2002_03
特許番号
US06355798B1

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