Hydrochloric Acid → HCID 59000877, compound

HRID 529166Notes

Reaction equation

HRID 529166 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[C:12]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:13]([N:28]([CH2:34][C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[S:14][C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][O:26][CH3:27])=[O:24])=[CH:18][CH:17]=1)C)C1C=CC=CC=1.Cl>C(O)C.[C].[Pd]>[F:42][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]([F:41])[C:35]=1[CH2:34][N:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:13]1[S:14][C:15]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][O:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)=[C:11]([CH2:10][NH:8][CH3:1])[C:12]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18324806HCID 18324806, compound

Product 1

HCID 59000877HCID 59000877, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(N-benzyl-N-methylaminomethyl)-2-[N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino]-5-[4-(3-methoxyureido)phenyl]thiophene-3-carboxylate (3.64 g, 5.47 mmol) in ethanol (100 ml) were added 1N hydrochloric acid (8 ml) and 10% palladium-carbon (50% wet, 1.82 g). The mixture was stirred vigorously under hydrogen atmosphere for 6 hours. The catalyst was removed, and the filtrate was neutralized with 1N sodium hydroxide solution. The solvent was distilled off, and the residue was distributed between ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to an NH-silica gel (Fuji Silysia Chemical) chromatography to give the title compound (2.43 g, 77%) as yellow powders.

Workup

  1. customThe catalyst was removed
  2. distillationThe solvent was distilled off
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c73102e78cee47408c3075d5b0d8f0e5
Source dataset
uspto-grants-2016_05
Patent number
US09346822B2

Reaction notes

Loading…