Water → 4-(2-Methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-7-(2-oxoethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361283Notes

Reaction equation

HRID 2361283 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N:24]5[C:33](=[O:34])[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[N:26]=[CH:25]5)[C:19]=4[CH3:35])=[CH:16][N:15]=[C:14]([C:36]([NH2:38])=[O:37])[C:10]=3[NH:11]2)=[CH:7][CH:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].O>ClCCl.O1CCCC1>[CH3:35][C:19]1[C:20]([N:24]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25]2)=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]1[C:9]2[C:8]3[C:12](=[CH:13][C:5]([O:4][CH2:3][CH:2]=[O:1])=[CH:6][CH:7]=3)[NH:11][C:10]=2[C:14]([C:36]([NH2:38])=[O:37])=[N:15][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 866815177-(2-Hydroxyethoxy)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

Product 1

HCID 866815184-(2-Methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-7-(2-oxoethoxy)-9H-pyrido[3,4-b]indole-1-carboxamideYield 118%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(2-hydroxyethoxy)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide (152 mg, 0.301 mmol) in dichloromethane (10 mL) and tetrahydrofuran (10.00 mL) at room temperature was added Dess-Martin periodinane (191 mg, 0.451 mmol) in one portion. The mixture was stirred at room temperature for 16 hr. To the mixture was added saturated NaHCO3 solution (10 mL) and water (10 mL). The mixture was stirred at room temperature for 20 min and extracted with ethyl acetate (3×40 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (178 mg, 0.354 mmol, 118% yield) as a beige solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 min
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. extractionThe combined extract
  4. washwas washed with brine (30 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-34421f9c73c14ffb82adf7faa3b5d676
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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