Hydrochloric Acid → HCID 53388810, compound

HRID 529168Notes

Reaction equation

HRID 529168 reaction equation
Cl.[F:2][C:3]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:4]=1[CH2:5][N:6]([C:12]1[S:13][C:14]([C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=2)=[C:15]([CH2:22][N:23]([CH2:25][CH2:26][O:27][CH3:28])[CH3:24])[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(OCC)C.C(O)C.[C].[Pd]>[F:2][C:3]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:4]=1[CH2:5][N:6]([C:12]1[S:13][C:14]([C:29]2[CH:30]=[CH:31][C:32]([NH2:35])=[CH:33][CH:34]=2)=[C:15]([CH2:22][N:23]([CH2:25][CH2:26][O:27][CH3:28])[CH3:24])[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 18324796HCID 18324796, compound

Product 1

HCID 53388810HCID 53388810, compoundYield 96.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2N hydrochloride in diethyl ether (21 ml) and 10% palladium-carbon (50% wet, 3.73 g) were added to a solution of ethyl 2-[N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino]-4-[N-(2-methoxyethyl)-N-methylaminomethyl]-5-(4-nitrophenyl)thiophene-3-carboxylate (12.43 g) (JP-A-2001-278884, WO 00/56739) in ethanol (315 ml). The mixture was stirred vigorously under hydrogen atmosphere for 1 hour. The catalyst was removed, and the filtrate was neutralized with sodium hydrogen carbonate 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 (11.44 g) as an oil.

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-ed5c325d4b864f8c8db0d56062070f7f
Source dataset
uspto-grants-2016_05
Patent number
US09346822B2

Reaction notes

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