HCID 90280613, compound → HCID 90280433, compound

HRID 57759Notes

Reaction equation

HRID 57759 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-])=O)[C:18]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:37])[NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])[CH:25]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1>C(OCC)C.[Pd]>[NH2:21][C:19]1[C:18]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:37])[NH:31][C:32]([CH3:35])([CH3:36])[CH2:33][OH:34])[CH:25]=2)=[CH:17][C:11]2[C:12]([C:13]([NH:15][CH3:16])=[O:14])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:9][C:10]=2[CH:20]=1

Participants

4

Reactant 1

HCID 90280613HCID 90280613, compound

Product 1

HCID 90280433HCID 90280433, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-5-(3-((1-hydroxy-2-methylpropan-2-yl)carbamoyl)phenyl)-N-methyl-6-nitrobenzofuran-3-carboxamide (108 mg) in ethyl ether (4 mL), was added palladium on carbon (1.137 mg). The mixture was stirred under hydrogen with a balloon for 16 hours. Pd/C was removed by filtration and the filtrate was concentrated to give 6-amino-2-(4-fluorophenyl)-5-(3-((1-hydroxy-2-methylpropan-2-yl)carbamoyl)phenyl)-N-methylbenzofuran-3-carboxamide 103 (95 mg).

Workup

  1. customPd/C was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7bb20715b3e44a2eb2f1fd77b8f73ebc
Source dataset
uspto-grants-2016_09
Patent number
US09434738B2

Reaction notes

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