Sodium Bicarbonate → HCID 67388281, compound

HRID 905651Notes

Reaction equation

HRID 905651 reaction equation
C(OCC)(=O)C.Cl.C(OC([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH:31]([NH:38][C:39]([NH:41][CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:40])[CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[CH:27][N:26]=1)=[O:24])=O)(C)(C)C.C(=O)([O-])O.[Na+]>CO>[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH:31]([NH:38][C:39]([NH:41][CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[O:40])[CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[CH:27][N:26]=1)=[O:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 67387749HCID 67387749, compound

Product 1

HCID 67388281HCID 67388281, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.0 M hydrogen chloride-ethyl acetate solution (1.0 mL) was added to a solution of N-(2-t-butoxycarbonylaminophenyl)-5-[1-(3-dimethylaminopropyl)-3-phenethylureidomethyl]pyridine-2-carboxylic acid amide (Reference Compound No. 6-1, 31 mg, 0.060 mmol) in methanol (2.0 mL), and then the reaction mixture was stirred at room temperature for 4 hours. Saturated aqueous sodium hydrogen carbonate solution (30 mL) was added thereto, and then the whole was extracted with ethyl acetate (30 mL) three times. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 24 mg of the title compound as a yellow amorphous product. (Yield 84%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (30 mL) three times
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-666b6363a0e94218a922e47556890264
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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