Sodium Nitrite → 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline

HRID 1892427ノート

反応式

HRID 1892427 の反応式
[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[C:11]([F:21])=[C:12]3[C:17](=[CH:18][C:19]=2[F:20])[N:16]=[CH:15][CH:14]=[CH:13]3)[C:5]([NH2:22])=[N:4][CH:3]=1.[N:23]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:9][C:10]3[C:11]([F:21])=[C:12]4[C:17](=[CH:18][C:19]=3[F:20])[N:16]=[CH:15][CH:14]=[CH:13]4)[N:23]=[N:22][C:5]2=[N:4][CH:3]=1

参加物

5

反応物 2

HCID 23668193Sodium NitriteHCID 866520516-bromo-N2-(5,7-difluoroquinolin-6-ylmethyl)pyrazine-2,3-diamine

生成物 1

HCID 866520526-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline収率 66%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

実験手順

To a solution of 6-bromo-N2-(5,7-difluoroquinolin-6-ylmethyl)pyrazine-2,3-diamine (1.5 g, 4.10 mmol) in acetic acid (50 mL) and water (10 mL) was added a solution of sodium nitrite (283 mg, 4.10 mmol) in water (3 mL). After stirring at it for 3 h, the solvent was removed in vacuo, the residue was taken with NaHCO3 (aq.), extracted with CH2Cl2. The organic layer was washed with NH4Cl (aq.), dried over Na2SO4, filtered and concentrated in vacuo and purified by silica gel chromatography with hexanes:EtOAc to provide 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline (1.02 g, 65%). 1H-NMR (400 MHz, CDCl3) δ ppm 8.99 (d, 1H), 8.79 (s, 1H), 8.43 (d, 1H), 7.65 (d, 1H), 7.49 (m, 1H), 6.13 (s, 2H). LCMS (method B): [MH]+=376.8, tR=2.23 min.

後処理

  1. customthe solvent was removed in vacuo
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with NH4Cl (aq.)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography with hexanes

出典と根拠

ORDレコード
ord-a7fff84b8d5a4eada1dede25659114f7
出典データセット
uspto-grants-2013_08
特許番号
US08507676B2

反応ノート

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