Hydrochloric Acid → 3-(2-Methoxyethoxy)-6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

HRID 1511394ノート

反応式

HRID 1511394 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([CH2:16][C:17](OC(C)(C)C)=O)=[CH:11][CH:10]=2.[C:24]1([C:30]2[N:35]=[N:34][C:33]([NH:36][NH2:37])=[CH:32][CH:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.[OH-].[Na+]>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([CH2:16][C:17]1[N:34]3[N:35]=[C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:31]=[CH:32][C:33]3=[N:36][N:37]=1)=[CH:11][CH:10]=2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 64098423-Hydrazinyl-6-phenylpyridazineHCID 57690925Tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate

生成物 1

HCID 576910723-(2-Methoxyethoxy)-6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To a 5 ml CEM microwave tube was added tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate (0.080 g, 0.25 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.094 g, 0.50 mmol), HYDROCHLORIC ACID (0.063 ml, 0.76 mmol), and water (0.2 mL) as solvent. The vial was sealed and first heated at 90° C. for 30 min then placed into CEM microwave for 15 min. at 140° C., with 100 Watts of power via Powermax. The reaction mixture was adjusted the pH to 7 by adding 5 N NaOH and the precipitate was collected via filtration. The brown ppt. was dissolved in DCM. The organic was washed with water, dried over MgSO4, and removed solvent in vacuo. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, DCM:EtOAc:MeOH=60%:37%:3%, Flow=30 mL/min) to afford the desired product as light yellowish solid. MS m/z: 412.3 (M+H). Calc'd. for C24H21N5O2—411.45.

後処理

  1. customThe vial was sealed
  2. filtrationthe precipitate was collected via filtration
  3. dissolutionwas dissolved in DCM
  4. washThe organic was washed with water
  5. dry with materialdried over MgSO4
  6. customremoved solvent in vacuo
  7. customThe crude product was purified

出典と根拠

ORDレコード
ord-0e99e1bb492e4b07bed6ff9c14894154
出典データセット
uspto-grants-2012_07
特許番号
US08212041B2

反応ノート

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