Tetrahydrofuran → HCID 54006151, compound

HRID 1284898Notes

Reaction equation

HRID 1284898 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:19](Cl)=[O:20])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].C(N([CH2:27][CH3:28])CC)C.[O:29]1CCCC1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:19]([O:20][CH2:27][CH3:28])=[O:29])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 54338259HCID 54338259, compound

Product 1

HCID 54006151HCID 54006151, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 150 mg of 8-chlorocarbonyl-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 19) in 5 ml of tetrahydrofuran is combined with a solution of triethylamine in ethanol at 4° C. until a pH of 8 is attained. The mixture is then stirred for 2 hours at room temperature and evaporated. After distribution in ethyl acetate/dilute ammonia solution, the organic phase is separated, dried, filtered, and concentrated. After chromatography over silica gel with methylene chloride/ethanol=10:1 as the eluent, 70 mg of 8-ethoxycarbonyl-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester is obtained.

Workup

  1. customevaporated
  2. customAfter distribution in ethyl acetate/dilute ammonia solution, the organic phase is separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa2d574cf4154391ab70ae1989485a96
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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