2-Aminobenzenesulfonamide → HCID 135495137, compound

HRID 494468Notes

Reaction equation

HRID 494468 reaction equation
CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:17].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH2:30])(=[O:29])=[O:28]>C1(C)C=CC=CC=1>[O:28]=[S:27]1(=[O:29])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20][C:3]([C:4]2[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[C:11]3[C:6]([C:5]=2[OH:17])=[CH:7][CH:8]=[CH:9][CH:10]=3)=[N:30]1

Participants

4

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 57604793HCID 57604793, compound

Product 1

HCID 135495137HCID 135495137, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 9G (450 mg) and 2-aminobenzenesulfonamide (180 mg, 1.05 mmol) in toluene (10 mL) was stirred at 100° C. for 2.5 hours, cooled to 25° C. and filtered. The filtrate was concentrated in vacuo, and the residue was chromatographed eluting with dichloromethane to give the title compound (57 mg, 15%). 1H NMR (300 MHz, CDCl3): δ 16.77, 16.61 (two s, 1 H), 14.36, 13.98 (two s, 1 H), 8.27 (m, 2 H), 7.99 (d, J=8.09 Hz, 2 H), 7.57 (m, 2 H), 7.31 (m, 2 H), 1.71 (s, 3 H), 1.56 (s, 3 H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was chromatographed
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c3702820a53141f3938b3a01a59b708f
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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