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Iodine → 3-((6-Chloro-3-cyanoimidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)benzoic acid

HRID 889472
ノート
印刷プレビュー

反応式

HRID 889472 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:14]2[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=2)[C:17]([O:19]C(C)(C)C)=[O:18])[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.II.O>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[C:14]2[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=2)[C:17]([OH:19])=[O:18])[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 807IodineHCID 962WaterHCID 59314053tert-Butyl 3-((6-chloro-3-cyanoimidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)benzoate

生成物 1

HCID 593140063-((6-Chloro-3-cyanoimidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)benzoic acid収率 66.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
80 °C

実験手順

A solution of 253B (100 mg, 0.20 mmol) in acetonitrile (5 mL) was treated with iodine (15.54 mg, 0.061 mmol) and water (50 μL, 2.78 mmol). The reaction mixture was stirred at 80° C. for 8 hours. The reaction mixture was diluted with ethyl acetate, and washed with water. The aqueous layer was extracted with ethyl acetate (4×20 mL). The pooled organic phase was dried over Na2SO4 and concentrated. The residue was triturated with DCM and filtered. The filtrate was concentrated, dissolved in DCM, and purified by flash chromatography, silica column (12 g, gradient elution from hexanes-ethyl acetate in 15 min.). The appropriate fraction was concentrated under reduced pressure and dried in vacuo to yield 253C (57.5 mg, 64.9% yield) as a yellow solid. HPLC: Rt=4.23 min. (PHENOMENEX® Luna C18 4.6×30 mm 3 u, A10-90% aqueous methanol containing 0.1% TFA in 2 min; 4 mL/min flow). MS (ES): m/z=434.0 [M+H]+.

後処理

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate (4×20 mL)
  3. dry with materialThe pooled organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was triturated with DCM
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. dissolutiondissolved in DCM
  9. custompurified by flash chromatography, silica column (12 g, gradient elution from hexanes-ethyl acetate in 15 min.)
  10. concentrationThe appropriate fraction was concentrated under reduced pressure
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-15d262f1fcc740d2aba008a3f14d52fc
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08252795B2

反応ノート

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