HCID 10412743, compound → 7-Amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide

HRID 1986643Notes

Reaction equation

HRID 1986643 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:8]([O:26][CH3:27])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([N+:23]([O-])=O)=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[C:8]([O:26][CH3:27])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([NH2:23])=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10412743HCID 10412743, compound

Product 1

HCID 103435957-Amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amideYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-nitro-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (1.2 g) in EtOAc (60 mL) was added 600 mg of 10% Pd/C. The reaction mixture was degassed and charged with H2 two times. The reaction was then stirred at room temperature under the H2 balloon. After 5 h, the reaction was diluted with EtOAc, filtered through a pad of diatomaceous earth and rinsed with EtOAc. The combined organics were concentrated to give 7-amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (1.1 g, 93%).

Workup

  1. customThe reaction mixture was degassed
  2. additioncharged with H2 two times
  3. additionthe reaction was diluted with EtOAc
  4. filtrationfiltered through a pad of diatomaceous earth
  5. washrinsed with EtOAc
  6. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-30f55410ce3441a595b1f15ece9c3c2d
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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