Sodium Bicarbonate → HCID 22097348, compound

HRID 1458993Notes

Reaction equation

HRID 1458993 reaction equation
[ClH:1].[CH3:2][C:3]1[N:7]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:6]=[CH:5][C:4]=1/[CH:14]=[CH:15]/[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[CH2:19][CH2:18]1.C(=O)([O-])[OH:32].[Na+]>Cl>[ClH:1].[CH3:2][C:3]1[N:7]([C:8]2[N:9]=[CH:10][CH:11]=[CH:12][N:13]=2)[N:6]=[CH:5][C:4]=1/[CH:14]=[CH:15]/[CH2:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29](=[O:32])[NH2:30])[CH:24]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22097334HCID 22097334, compound

Product 1

HCID 22097348HCID 22097348, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

88 mg of the compound obtained in Example 32 (3) was dissolved in 0.5 ml of conc. hydrochloric acid and stirred at room temperature for 62 hours. Then the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (chloroform:methanol=100:3). Then the product was converted into hydrochloride with a 1N hydrochloric acid/ethanol solution and recrystallized from ethanol. Thus 50 mg of the title compound was obtained in the form of colorless crystals.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter evaporating the solvent
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:3)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d280721a36264d59b0d8ac7d4c9eb2a4
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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