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Dimethylformamide → N-Hydroxy-3-[1-(4-methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-N-methylpropanamide Monoformate

HRID 5016
ノート
印刷プレビュー

反応式

HRID 5016 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[CH:13][C:12]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[N:11]2)=[CH:6][CH:5]=1.[CH3:26][N:27]([CH:29]=[O:30])C.C(Cl)(=O)C(Cl)=[O:33]>C(Cl)Cl>[CH:23]([OH:25])=[O:24].[OH:33][N:27]([CH3:26])[C:29](=[O:30])[CH2:22][CH2:21][C:12]1[CH:13]=[C:14]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=2)[N:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 678573363-[1-(4-Methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-propionic acid hydrochloride

生成物 1

HCID 19797563N-Hydroxy-3-[1-(4-methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-N-methylpropanamide Monoformate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of compound 31 (0.9 g, 2 5 mM) in CH2Cl2 (25 ml) at RT was added DMF (0.2 ml) and oxalyl chloride (1.26 g, 10 mM). After stirring for 0.5 hr, the reaction mixture was evaporated in vacuo, redissolved in CH2Cl2 (25 ml) and added dropwise to a solution of methylhydroxylamine hydrochloride (0.84 g, 10 mM) and Et3N (3.7 ml) in CH2Cl2 (50 ml) at 0° C. The reaction was stirred for 10 min and poured into a 1:1 stirred mixture of Ch2Cl2 :H2O. The CH2Cl2 layer was separated, washed (H2O and then brine), dried (Na2SO4) and evaporated in vacuo to give a semi-solid which was purified by column chromatography on Silica employing Hexane:40EtOAc:1% MeOH:0.1% HCO2H as eluent. The title compound 35 was obtained as a tan foam as the monoformate salt; MS, m/e 352 (M+).

後処理

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionredissolved in CH2Cl2 (25 ml)
  3. additionadded dropwise to a solution of methylhydroxylamine hydrochloride (0.84 g, 10 mM) and Et3N (3.7 ml) in CH2Cl2 (50 ml) at 0° C
  4. stirringThe reaction was stirred for 10 min
  5. additionpoured into a 1:1
  6. stirringstirred
  7. additionmixture of Ch2Cl2
  8. customThe CH2Cl2 layer was separated
  9. washwashed (H2O
  10. dry with materialbrine), dried (Na2SO4)
  11. customevaporated in vacuo
  12. customto give a semi-solid which
  13. customwas purified by column chromatography on Silica

出典と根拠

ORDレコード
ord-8a523d4abd2d452793523bb1a14f206d
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05242940

反応ノート

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