Acetic Acid → 6-[1,2,3]Triazolo[4,5-b]pyrazin-1-ylmethyl-quinoline

HRID 15996

反応式

HRID 15996 の反応式
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.CC(O)=O.CCOC(C)=O.[H][H]>CO.[Pd]>[N:8]1([CH2:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[C:6]2=[N:7][CH:2]=[CH:3][N:4]=[C:5]2[N:10]=[N:9]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 593419336-[1,2,3]Triazolo[4,5-b]pyrazin-1-ylmethyl-quinoline収率 20%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 887Methanol溶媒

実験手順

A solution of 6-(6-bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinoline (200 mg, 0.586 mmol) in MeOH (10 mL):AcOH (1 mL): EtOAc (1 mL) was degassed 3 times with nitrogen. To this solution was added Pd/C (20 mg). A balloon containing hydrogen was added via syringe and the reaction was allowed to stir for 18 hours at room temperature. The reaction did not complete and more Pd/C was added (20 mg) and stirred for 18 hours at room temperature. The reaction was stopped when LCMS showed a ratio of 1:1 (product:starting material). The reaction was filtered over celite and washed with EtOAc (50 mL). The filtered solution was concentrated and purified by Biotage silica gel column chromatography with EtOAc: Hexanes to give 30 mg of the product 6-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl-quinoline (20% yield).

後処理

  1. additionwas added via syringe
  2. stirringstirred for 18 hours at room temperature
  3. filtrationThe reaction was filtered over celite
  4. washwashed with EtOAc (50 mL)
  5. concentrationThe filtered solution was concentrated
  6. custompurified by Biotage silica gel column chromatography with EtOAc

出典と根拠

ORDレコード
ord-4825ae5a95894914b5d5be85049a19ca
出典データセット
uspto-grants-2010_06
特許番号
US07732604B2

関連ノート

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