1,2-Dichloroethane → HCID 10412743, compound

HRID 1986642Notes

Reaction equation

HRID 1986642 reaction equation
[N+:1]([C:4]1[C:9]2[S:10][C:11]([C:13]([OH:15])=O)=[CH:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:30][C:31]1[C:32]([O:46][CH3:47])=[C:33]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH:34]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:36]=1>CN(C=O)C>[C:37]([C:35]1[CH:34]=[C:33]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[C:32]([O:46][CH3:47])=[C:31]([NH:30][C:13]([C:11]2[S:10][C:9]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[CH:12]=2)=[O:15])[CH:36]=1)([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 131624097-Nitrobenzo[b]thiophene-2-carboxylic acid

Product 1

HCID 10412743HCID 10412743, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the above carboxylic acid (900 mg) in DMF was added EDC (1.2 eq) and HOBT (1.2 eq). After stirring for 10 min, N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (1.0 eq) was added. The suspension was stirred at room temperature for 48 h. The DMF was removed in vacuo and the resulting oil was dissolved in EtOAc, washed with water three times, followed by saturated NaHCO3 solution and brine. The organics were dried over MgSO4, filtered and concentrated to give a crude yellow solid which was triturated with 30% EtOAc/hex (small amount) and filtered to provide 7-nitro-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide as a bright yellow solid (1.4 g, 72%).

Workup

  1. stirringThe suspension was stirred at room temperature for 48 h
  2. customThe DMF was removed in vacuo
  3. dissolutionthe resulting oil was dissolved in EtOAc
  4. washwashed with water three times
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude yellow solid which
  9. customwas triturated with 30% EtOAc/hex (small amount)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ed110744363446d0b3ef6cf5da8fdbff
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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