4-Amino-2-methylpyridine → 6-chloro-8-((4-methoxybenzyl)(phenyl)amino)-N-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

HRID 1943498

反応式

HRID 1943498 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[N:6]([C:8]([C:11](O)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:30][C:31]1[CH:36]=[C:35]([NH2:37])[CH:34]=[CH:33][N:32]=1>O=S(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[N:6]([C:8]([C:11]([NH:37][C:35]3[CH:34]=[CH:33][N:32]=[C:31]([CH3:30])[CH:36]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1

参加物

4

反応物 2

HCID 7286704-Amino-2-methylpyridineHCID 596248836-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carboxylic acid

生成物 1

HCID 596246286-chloro-8-((4-methoxybenzyl)(phenyl)amino)-N-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide収率 55.2%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

6-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carboxylic acid (150 mg, 0.37 mmol) in SOCl2 (2 mL) was heated at 60° C. for 1 hour. The reaction mixture was concentrated, dried under reduced pressure and dissolved in DCM (3 mL). 2-Methylpyridin-4-amine (45 mg, 0.41 mmol), and TEA (0.16 mL, 1.11 mmol) were added and the reaction mixture was stirred at room temperature for 12 hours, concentrated and then purified by silica gel chromatography (5% MeOH in DCM) to obtain 6-chloro-8-((4-methoxybenzyl)(phenyl)amino)-N-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide (102 mg, 55% yield) as a yellow solid. LC/MS (Phenomenex Luna 5 micron C18 4.6×30 mm, 0 to 100 B in 2 min with 1 min hold time, Flow rate=5 mL/min, detection at 254 nm, Solvent A: 10% methanol/90% water/0.1% TFA; Solvent B: 10% water/90% methanol/0.1% TFA). Rt=3.263 minutes. [M+H]=499.06.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customdried under reduced pressure
  3. dissolutiondissolved in DCM (3 mL)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (5% MeOH in DCM)

出典と根拠

ORDレコード
ord-e7c76ce73f8743a69e35bb53641aa026
出典データセット
uspto-grants-2013_03
特許番号
US08389527B2

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