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

반응식

HRID 277333 반응식
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

참가 물질

4

반응물 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

생성물 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]pyridazine수율 26.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
150 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-983a399c0c574c15a5e782ea01d8e685
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355798B1

연결된 노트

불러오는 중…