Cyclohexene oxide → 7,8-Bis(4-chlorophenyl)-2-(2-hydroxycyclohexyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224211노트

반응식

HRID 2224211 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[CH:25]12[O:31][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[N:15]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]4[OH:31])[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 9246Cyclohexene oxideHCID 11430Potassium CarbonateHCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

생성물 1

HCID 597167657,8-Bis(4-chlorophenyl)-2-(2-hydroxycyclohexyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (40 mg, 0.11 mmol), prepared as described in Example 1, cyclohexene oxide (12 mg, 0.12 mmol) and K2CO3 (35 mg, 0.25 mmol) in DMF (1 ml), was heated at 100° C. for 3 hours. After this time the solution was cool to RT and diluted with ethyl acetate. The resultant solution was washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(2-hydroxycyclohexyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-(24.1 mg, 48%) as yellow solid. MS M+H=455; 1H NMR (CDCl3) δ 8.17 (1H), 7.33 (6H), 7.08 (2H), 4.26 (1H), 3.98 (1H), 2.17 (1H), 1.99 (1H), 1.82 (3H), 1.50-1.30 (3H).

후처리

  1. temperatureAfter this time the solution was cool to RT
  2. washThe resultant solution was washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-0ba9d2fa1f2f4309b1c36ab01a2a1960
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378418B2

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