Sodium Hydroxide → N,N-dimethyl-2-(6((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolin-3-yloxy)ethanamine

HRID 40303

반응식

HRID 40303 반응식
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][C:21]([OH:27])=[CH:20]5)=[N:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.Cl[CH2:32][CH2:33][N:34]([CH3:36])[CH3:35].[OH-].[Na+]>CN(C=O)C>[CH3:35][N:34]([CH3:36])[CH2:33][CH2:32][O:27][C:21]1[CH:22]=[N:23][C:24]2[C:19]([CH:20]=1)=[CH:18][C:17]([CH2:16][C:13]1[N:11]3[N:12]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=[CH:9][C:10]3=[N:15][N:14]=1)=[CH:26][CH:25]=2

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 576913296-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolin-3-ol

생성물 1

HCID 57691121N,N-dimethyl-2-(6((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolin-3-yloxy)ethanamine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolin-3-ol (0.05 g, 0.1 mmol) was dissolved in DMF (8 mL). SODIUM HYDRIDE (0.01 g, 0.3 mmol) was added and allowed to stir for 1 h at rt. 2-chloro-N,N-dimethylethanamine hydrochloride (0.06 g, 0.4 mmol), which was free-based using 5 N NaOH then extracted with ether, was added. The resulting mixture was continued to stir for 20 h at rt. Solvent was removed in vacuo. The crude material was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, solvent system: DCM:MeOH(2M NH3)=95%:5%, Flow=30 mL/min) to afford the title compound MS m/z: 425.3 (M+H). Calc'd. for C25H24N6O—424.49.

후처리

  1. extractionthen extracted with ether
  2. additionwas added
  3. stirringto stir for 20 h at rt
  4. customSolvent was removed in vacuo
  5. customThe crude material was purified

출처 및 근거

ORD 기록
ord-c7d726a56487461bb65998b96cae2431
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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