3,4-diaminobenzenesulfonamide → HCID 10068962, compound

HRID 2054466Notes

Reaction equation

HRID 2054466 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:4][C:3]=1[CH:16]=O.[NH2:18][C:19]1[CH:20]=[C:21]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[NH2:25].OS([O-])=O.[Na+]>CC(N(C)C)=O>[NH2:1][C:2]1[C:3]([C:16]2[NH:18][C:19]3[CH:20]=[C:21]([S:26]([NH2:29])(=[O:27])=[O:28])[CH:22]=[CH:23][C:24]=3[N:25]=2)=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][CH:13]=[C:10]([C:11]#[N:12])[CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 27359273,4-diaminobenzenesulfonamideHCID 23665763Sodium BisulfiteHCID 58668627HCID 58668627, compound

Product 1

HCID 10068962HCID 10068962, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C

Procedure

3-(6-amino-5-formylpyridin-3-yl)benzonitrile (0.06 g, 0.27 mmol), 3,4-diaminobenzene-1-sulphonamide (0.050 g, 0.27 mmol), and NaHSO3 (0.029, 0.40 mmol) were combined in 2 mL of dimethylacetamide and heated to 200° C. in the SmithSynthesizer™ microwave instrument for 10 minutes. Upon cooling, the solvent was removed and the residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (0 to 100% EtOAc over 10 minutes) to afford 2-[2-amino-5-(3-cyanophenyl)pyridin-3-yl]-1H-benzimidazole-6-sulfonamide (0.046 g) as a solid.

Workup

  1. temperatureUpon cooling
  2. customthe solvent was removed
  3. customthe residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (0 to 100% EtOAc over 10 minutes)

Sources & evidence

ORD record
ord-d7fe3d9d55394ba59c4bc82294e406c8
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

Loading…