1,2-Dichloroethane → 4-Nitro-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide

HRID 1986653Notes

Reaction equation

HRID 1986653 reaction equation
[N+:1]([C:4]1[C:12]2[CH:11]=[C:10]([C:13]([OH:15])=O)[S:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:16][C:17]1[C:18]([O:32][CH3:33])=[C:19]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:23]([C:21]1[CH:20]=[C:19]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:18]([O:32][CH3:33])=[C:17]([NH:16][C:13]([C:10]2[S:9][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=3[CH:11]=2)=[O:15])[CH:22]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 221233224-Nitrobenzo[b]thiophene-2-carboxylic acid

Product 1

HCID 117547814-Nitro-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amideYield 25.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitro-benzo[b]thiophene-2-carboxylic acid (369 mg, 1.65 mmol) and N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (500 mg, 1.84 mmol) were dissolved in 25 mL DMF and stirred at room temperature. After about 10 min, EDC (317 mg, 1.65 mmol) and HOBt (224 mg, 1.65 mmol) were added and the brown solution was stirred at room temperature 12 h. After stirring 12 h, the reaction was partitioned between EtOAc (150 mL) and water (50 mL). The layers were separated and the organic portion was washed with water (2×25 mL), brine (25 mL), dried (MgSO4), filtered and the solvent was removed in vacuo to afford a brown solid. Column chromatography on silica gel afforded 4-nitro-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide as a pale yellow solid (200 mg, 25%).

Workup

  1. stirringthe brown solution was stirred at room temperature 12 h
  2. stirringAfter stirring 12 h
  3. customthe reaction was partitioned between EtOAc (150 mL) and water (50 mL)
  4. customThe layers were separated
  5. washthe organic portion was washed with water (2×25 mL), brine (25 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customto afford a brown solid

Sources & evidence

ORD record
ord-342d72c47aad43e6a793d487918d5300
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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