Sulfamide → Phenyl-1,3-dihydro-2-thia-1,3,9-triaza-cyclopenta[a]naphthalene 2,2-dioxide

HRID 513810Notes

Reaction equation

HRID 513810 reaction equation
[S:1](N)(N)(=[O:3])=[O:2].[C:6]1([NH:12][C:13]2[C:22]([NH2:23])=[C:21]3[C:16](C=CC=N3)=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1>[C:6]1([N:12]2[C:13]3=[C:14]4[C:15](=[CH:16][CH:21]=[C:22]3[NH:23][S:1]2(=[O:3])=[O:2])[CH:8]=[CH:7][CH:6]=[N:12]4)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 131733285N*7*-Phenyl-quinoline-7,8-diamine

Product 1

HCID 68183426Phenyl-1,3-dihydro-2-thia-1,3,9-triaza-cyclopenta[a]naphthalene 2,2-dioxideYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

Sulfamide (34 mg, 0.35 mmol) was added to a solution of N*7*-phenyl-quinoline-7,8-diamine 576 (56 mg, 0.23 mmol) in pyridine (2 ml) and the mixture was heated in a microwave at 115° C. for 2 h. After cooling, the solvent was removed in vacuo. The residue was dissolved in EtOAc (50 ml) and the organic phase was washed with sat. NaHCO3 solution (30 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography DCM/MeOH/TEA (98:2:0.5-90:10:0.5 gradient) followed by preparative HPLC (acidic conditions 1) to give the title compound (12.3 mg, 17%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (50 ml)
  4. washthe organic phase was washed with sat. NaHCO3 solution (30 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography DCM/MeOH/TEA (98:2:0.5-90:10:0.5 gradient)

Sources & evidence

ORD record
ord-23ff1a25bec241e8a2fca1b5e5e9c09b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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