Ethyl Acetate → HCID 44513518, compound

HRID 217641Notes

Reaction equation

HRID 217641 reaction equation
C(OCC)(=O)C.Cl.C(OC([NH:15][C:16]1[C:17]([NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:45][CH2:46][N:47]([CH3:49])[CH3:48])[C:32]([NH:34][C:35]3[CH:44]=[CH:43][C:38]4[O:39][CH2:40][CH2:41][O:42][C:37]=4[CH:36]=3)=[O:33])=[CH:26][N:25]=2)=[O:23])=[CH:18][S:19][CH:20]=1)=O)(C)(C)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CO>[NH2:15][C:16]1[C:17]([NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:45][CH2:46][N:47]([CH3:49])[CH3:48])[C:32]([NH:34][C:35]3[CH:44]=[CH:43][C:38]4[O:39][CH2:40][CH2:41][O:42][C:37]=4[CH:36]=3)=[O:33])=[CH:26][N:25]=2)=[O:23])=[CH:18][S:19][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 67049699HCID 67049699, compound

Product 1

HCID 44513518HCID 44513518, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

4.0 M Hydrogen chloride-ethyl acetate solution (5.0 mL) was added to a solution of N-(4-t-butoxycarbonylaminothiophen-3-yl)-5-[3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-1-(2-dimethylaminoethyl)ureidomethyl]pyridine-2-carboxylic acid amide (Reference Compound No. 6-4, 60 mg, 0.10 mmol) in a mixed solvent of ethyl acetate (2.0 mL)-methanol (3.0 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Chloroform (0.10 L) and saturated aqueous sodium hydrogen carbonate solution (0.15 L) were added to a reaction solution, and then the whole was partitioned. The organic layer was washed with brine (0.10 L). The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to give 38 mg of the title compound as an orange amorphous product. (Yield 77%)

Workup

  1. customthe whole was partitioned
  2. washThe organic layer was washed with brine (0.10 L)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-093f883506e24b10892cd61de46f4413
Source dataset
uspto-grants-2012_06
Patent number
US08198271B2

Reaction notes

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