Diethylethanolamine → HCID 10428091, compound

HRID 1376121Notes

Reaction equation

HRID 1376121 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 10428091HCID 10428091, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7bee938389b14ceab8db2b1cf8a30961
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

Loading…