Water → 8-Methyl-6-(3-methyloxetan-3-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 217677

反応式

HRID 217677 の反応式
[CH3:1][C:2]1([CH2:6][OH:7])[CH2:5][O:4][CH2:3]1.[H-].[Na+].Br.Cl[C:12]1[CH:13]=[C:14]([CH3:22])[C:15]2[N:16]([C:18]([NH2:21])=[N:19][N:20]=2)[N:17]=1.O>CN(C=O)C>[CH3:22][C:14]1[C:15]2[N:16]([C:18]([NH2:21])=[N:19][N:20]=2)[N:17]=[C:12]([O:7][CH2:6][C:2]2([CH3:1])[CH2:5][O:4][CH2:3]2)[CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1378373-Methyl-3-oxetanemethanolHCID 866507966-Chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

生成物 1

HCID 581368118-Methyl-6-(3-methyloxetan-3-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine収率 53.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
45 °C

実験手順

(3-Methyloxetan-3-yl)methanol (1.74 g) was initially charged in DMF (30 ml), admixed under argon with sodium hydride (408 mg) and stirred at 45° C. for 0.5 h. Subsequently, 6-chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.002; 1.5 g) was dissolved in DMF (30 ml) and one equivalent of the alkoxide solution (10 ml) was added. After stirring at 45° C. for 30 min, a further 0.5 equivalent of alkoxide solution was added, followed by 0.5 eq. each after a further 30 and 60 min. Then the mixture was admixed with water, and the reaction mixture was dried and purified using silica gel (80 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min). 758 mg of the title compound were obtained. LC-MS rt: 0.49 min [M+H]+: 250.1 (met. b)

後処理

  1. stirringAfter stirring at 45° C. for 30 min
  2. customafter a further 30 and 60 min
  3. customthe reaction mixture was dried
  4. custompurified
  5. customsilica gel (80 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min)

出典と根拠

ORDレコード
ord-be4cfa6efe2d4b378b756474706e0cb0
出典データセット
uspto-grants-2012_06
特許番号
US08198272B2

関連ノート

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