Sodium Hydroxide → 3-[3-(5-Bromo-3-methylpyrid-2-yl)propyl]-6-(3-pyridylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine

HRID 1607049ノート

反応式

HRID 1607049 の反応式
[N:1]([O-])=O.[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH3:30])[C:9]([CH2:12][CH2:13][CH2:14][NH:15][C:16]2[C:21]([NH2:22])=[CH:20][C:19]([CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:18][N:17]=2)=[N:10][CH:11]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:7]=[C:8]([CH3:30])[C:9]([CH2:12][CH2:13][CH2:14][N:15]2[C:16]3=[N:17][CH:18]=[C:19]([CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:20]=[C:21]3[N:22]=[N:1]2)=[N:10][CH:11]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 198517762-[3-(5-Bromo-3-methylpyrid-2-yl)-propylamino]-3-amino-5-(pyrid-3-ylmethyl)pyridineHCID 23668193Sodium Nitrite

生成物 1

HCID 198517903-[3-(5-Bromo-3-methylpyrid-2-yl)propyl]-6-(3-pyridylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine収率 57%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

Sodium nitrite solution (1.02 g in 50 ml water) was added dropwise over 25 minutes to a stirred and cooled solution of 2-[3-(5-bromo-3-methylpyrid-2-yl)-propylamino]-3-amino-5-(pyrid-3-ylmethyl)pyridine (4.7 g) in sulphuric acid (molar, 200 ml) keeping the temperature at 4° C. Reaction was stirred at 4° C. for a further hour and was then left in the fridge overnight and then warmed to room temperature. The reaction mixture was basified to pH 13 with sodium hydroxide solution (10 M). Chloroform extraction of the reaction mixture gave the crude product which was then chromatographed on silica in methanol/chloroform 1:19 and then recrystallised from acetonitrile to give the title compound (2.75 g), m.p. 109°-110° C.

後処理

  1. customat 4° C
  2. customReaction
  3. stirringwas stirred at 4° C. for a further hour
  4. extractionChloroform extraction of the reaction mixture
  5. customgave the crude product which
  6. customwas then chromatographed on silica in methanol/chloroform 1:19
  7. customrecrystallised from acetonitrile

出典と根拠

ORDレコード
ord-235d2c5d355c42e8930c9cc34fd311f8
出典データセット
uspto-grants-1989_09
特許番号
US04863933

反応ノート

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