3-Hydrazinyl-6-phenylpyridazine → 3-Methoxy-6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

HRID 40212

반응식

HRID 40212 반응식
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH2:13][C:14](OC(C)(C)C)=O)=[CH:8][CH:7]=2.[C:21]1([C:27]2[N:32]=[N:31][C:30]([NH:33][NH2:34])=[CH:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>Cl>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH2:13][C:14]1[N:31]3[N:32]=[C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:28]=[CH:29][C:30]3=[N:33][N:34]=1)=[CH:8][CH:7]=2

참가 물질

4

반응물 2

HCID 64098423-Hydrazinyl-6-phenylpyridazineHCID 59843087Tert-butyl 2-(3-methoxyquinolin-6-yl)acetate

생성물 1

HCID 576913553-Methoxy-6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
100 °C

실험 절차

A mixture of tert-butyl 2-(3-methoxyquinolin-6-yl)acetate (148 mg) and 1-(6-phenylpyridazin-3-yl)hydrazine (126 mg) in HCl (conc., 0.3 mL) was heated at 100° C. for 5 min and was subject to microwave heating (180° C., 15 min) The yellow sludge was quenched with NaOH (5N, 1 mL). The pink mixture was filtered and washed with NaOH (1 N, 1 mL), H2O (2 mL). The solid was suspended in DMF (2 mL)-DCM (2 mL). MeI (0.2 mL) was added followed by the addition of NaOH (2N, 1 mL). After 2 h, the mixture was partitioned between DCM (10 mL) and aqueous Na2SO3 (5 mL). The organic was dried over MgSO4, concentrated, and purified in silica (1-15% MeOH in DCM) to give the product as a yellow powder.

후처리

  1. temperatureheating (180° C., 15 min) The yellow sludge
  2. customwas quenched with NaOH (5N, 1 mL)
  3. filtrationThe pink mixture was filtered
  4. washwashed with NaOH (1 N, 1 mL), H2O (2 mL)
  5. additionMeI (0.2 mL) was added
  6. additionfollowed by the addition of NaOH (2N, 1 mL)
  7. customthe mixture was partitioned between DCM (10 mL) and aqueous Na2SO3 (5 mL)
  8. dry with materialThe organic was dried over MgSO4
  9. concentrationconcentrated
  10. custompurified in silica (1-15% MeOH in DCM)

출처 및 근거

ORD 기록
ord-ac00229e44b74023bf42debc5b683c56
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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