Ethylene Glycol → tert-Butyl 1-(4-(8-(2-hydroxyethoxy)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

HRID 1037427Notes

Reaction equation

HRID 1037427 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12.[CH2:37]([OH:40])[CH2:38][OH:39].CC(C)([O-])C.[K+]>CN(C=O)C>[OH:39][CH2:38][CH2:37][O:40][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 23665647Potassium tert-butoxideHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Product 1

HCID 67067725tert-Butyl 1-(4-(8-(2-hydroxyethoxy)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamateYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (50 mg, 0.099 mmol) in DMF (1 mL) were added ethane-1,2-diol (30.8 mg, 0.497 mmol) and potassium tert-butoxide (33.5 mg, 0.298 mmol) under nitrogen. The reaction mixture was stirred at RT overnight, followed by heating at 50° C. for 4 h. The product was extracted with ethyl acetate, washed with water, dried, and purified by chromatography to give the title compound (20 mg, 38%). LCMS (Method J): RT=1.493 min, [M+H]+=529.

Workup

  1. temperatureby heating at 50° C. for 4 h
  2. extractionThe product was extracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-41b32d15e264420db6f5ab69c385b9bd
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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