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Sodium 1-Methyl 3-Sulfinopropionate → 3-[5-(1-{[1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-cyclopropyl)-pyridine-2-sulfonyl]-propionic acid methyl ester

HRID 2172979
ノート
印刷プレビュー

反応式

HRID 2172979 の反応式
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:30][O:31][C:32](=[O:38])[CH2:33][CH2:34][S:35]([O-:37])=[O:36].[Na+]>CS(C)=O.[Cu]I>[CH3:30][O:31][C:32](=[O:38])[CH2:33][CH2:34][S:35]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:6][N:7]=1)(=[O:37])=[O:36]
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

5

反応物 2

HCID 23665669Sodium 1-Methyl 3-SulfinopropionateHCID 529167991-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide

生成物 1

HCID 529174263-[5-(1-{[1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-cyclopropyl)-pyridine-2-sulfonyl]-propionic acid methyl ester

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

A solution of 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide (0.250 g, 0.553 mmol), sodium 3-methoxy-3-oxopropane-1-sulfinate (289 mg, 1.66 mmol) and copper (I) iodide (316 mg, 1.66 mmol) in DMSO (2 mL) is placed in a microwave tube and evacuated and purged with argon three times. The reaction mixture is heated in a microwave at 110° C. for 2 hours, diluted with ethyl acetate (200 mL), washed with saturated aqueous ammonium chloride (4×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated. The resulting residue is purified by silica gel chromatography eluting with a gradient of 50-100% ethyl acetate in heptane to afford the title compound as a solid.

後処理

  1. customevacuated
  2. custompurged with argon three times
  3. additiondiluted with ethyl acetate (200 mL)
  4. washwashed with saturated aqueous ammonium chloride (4×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel chromatography
  9. washeluting with a gradient of 50-100% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-e61f11fda3cf4c0c9a225c6d3e119664
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056858B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート