Diethylethanolamine → HCID 10428091、化合物

HRID 1376121ノート

反応式

HRID 1376121 の反応式
[H-].[Na+].[CH2:3]([N:5]([CH2:9][CH3:10])[CH2:6][CH2:7][OH:8])[CH3:4].FC1C([O:18][C:19]([C:21]2[NH:22][C:23]3[C:28]([C:29]=2[NH:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)=O)=C(F)C(F)=C(F)C=1F>CN1CCCC1=O.CO.C(OCC)(=O)C>[CH2:3]([N:5]([CH2:9][CH3:10])[CH2:6][CH2:7][O:8][C:19]([C:21]1[NH:22][C:23]2[C:28]([C:29]=1[NH:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:18])[CH3:4]

参加物

6

反応物 3

HCID 7497DiethylethanolamineHCID 24758Sodium hydrideHCID 99794613-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Pentafluorophenyl Ester

生成物 1

HCID 10428091HCID 10428091、化合物収率 31.1%

試薬・触媒・溶媒 2

HCID 13387N-methyl-2-pyrrolidone溶媒HCID 21584119Ethylacetate methanol溶媒

反応条件

温度
0 °C

実験手順

Stir under N2 at 0° C. a suspension of NaH (29 mg, 0.72 mmol of 60% oil dispersion) in 1-methyl-2-pyrrolidinone (15 mL), and slowly add N,N-diethylethanolamine(0.095 mL, 0.72 mmol). Stir for 10 min and then add dropwise 3-(pyridin-4-ylamino)-1H-indole-2-carboxylic acid pentafluorophenyl ester (100 mg, 0.24 mmol). Allow the reaction to reach ambient temperature and stir overnight. Quench into water and extract with ethyl acetate. Wash the extract with water, brine, dry (MgSO4), filter and concentrate under vacuum to obtain crude product. Chromatograph on silica gel (10 g, Sepack cartridge) and use 1:1 methanol/ethyl acetate as eluent. Combine like fractions and concentrate under vacuum to obtain 26.3 mg (31%) of the titled compound: MS 353 (M+H).

後処理

  1. stirringStir for 10 min
  2. customthe reaction
  3. customto reach ambient temperature
  4. stirringstir overnight
  5. customQuench into water
  6. extractionextract with ethyl acetate
  7. washWash the
  8. extractionextract with water, brine
  9. dry with materialdry (MgSO4)
  10. filtrationfilter
  11. concentrationconcentrate under vacuum
  12. customto obtain crude product
  13. concentrationCombine like fractions and concentrate under vacuum

出典と根拠

ORDレコード
ord-7bee938389b14ceab8db2b1cf8a30961
出典データセット
uspto-grants-2007_01
特許番号
US07169925B2

反応ノート

読み込み中…