Methyl 4-(N-(benzyloxycarbonyl)benzofuran-2-carboxamido)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate → Methyl 4-(benzofuran-2-carboxamido)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

HRID 1918214Notes

Reaction equation

HRID 1918214 reaction equation
C(OC([N:11]([C:23]1[C:24]([C:36]([O:38][CH3:39])=[O:37])=[C:25]([C:28]2[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][N:29]=2)[S:26][CH:27]=1)[C:12]([C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[CH:18]=1)=[O:13])=O)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C.ClCCl.[Pd]>[O:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[CH:18]=[C:14]1[C:12]([NH:11][C:23]1[C:24]([C:36]([O:38][CH3:39])=[O:37])=[C:25]([C:28]2[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][N:29]=2)[S:26][CH:27]=1)=[O:13]

Participants

4

Reactant 1

HCID 67052367Methyl 4-(N-(benzyloxycarbonyl)benzofuran-2-carboxamido)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

Product 1

HCID 67052227Methyl 4-(benzofuran-2-carboxamido)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22027680Ethanol ethyl acetate methylene chlorideSolvent

Procedure

10% Pd/C is added to compound 160 in ethanol:ethyl acetate:dichloromethane (2:1:1). The mixture is degassed and placed under H2 (1 atm) and stirred for 30 min. The mixture is filtered through a 0.45 μm syringe filter and concentrated under reduced pressure to provide 161.

Workup

  1. customThe mixture is degassed
  2. filtrationThe mixture is filtered through a 0.45 μm syringe
  3. filtrationfilter
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd0c3852eb2646ac9d3053c18badbc35
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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