Sodium Bicarbonate → HCID 23019635, compound

HRID 1354196Notes

Reaction equation

HRID 1354196 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]3[C:16]([C:17]=2[CH3:18])=[C:15]([CH:19]2[CH2:21][CH2:20]2)[CH:14]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=[O:27])=[CH:4][CH:3]=1.[O-:28][C:29]#[N:30].[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[CH:19]1([C:15]2[CH:14]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12](=[O:27])[N:11]3[C:16]=2[C:17]([CH3:18])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:29]([NH2:30])=[O:28])=[CH:7][CH:6]=2)[CH:9]=[CH:10]3)[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 23019679HCID 23019679, compound

Product 1

HCID 23019635HCID 23019635, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

54 mg of ethyl 8-(4-aminophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 2) was dissolved in a mixture of 3 ml of acetic acid and 2 ml of water. 2 ml of an aqueous solution of 19 mg of sodium cyanate was added to the obtained solution at 35° C. and they were stirred at that temperature for 3 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution. After the extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain 53 mg of ethyl 1-cyclopropyl-9-methyl-4-oxo-8-(4-ureidophenyl)-4H-quinolizine-3-carboxylate.

Workup

  1. extractionAfter the extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-7e4c53b415664c50845e50ed56b79144
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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