Pyridine → Phenyl-8-quinolinesulfonamide

HRID 1064448Notes

Reaction equation

HRID 1064448 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11](Cl)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.N[C:16]1[CH:22]=[CH:21][C:20](N2CCN(C)CC2)=[CH:19][C:17]=1N.[N:30]1C=CC=CC=1>C(Cl)Cl>[C:16]1([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[C:9]([S:11]([NH2:30])(=[O:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 292208-Quinolinesulfonyl chlorideHCID 27635454-(4-Methylpiperazino)-1,2-benzenediamine

Product 1

HCID 86588921Phenyl-8-quinolinesulfonamideYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Quinolinesulfonyl chloride (0.185 g, 0.81 mmol) was added to a solution of 2-amino-5-(4-methyl-1-piperazinyl)aniline (0.168 g, 0.81 mmol) and pyridine (514 mL, 6.39 mmol) in CH2Cl2. After 1 h at room temperature the mixture was washed with aq NaHCO3 (10%), dried (MgSO4) and the solvent was removed. Purification by chromatography (SiO2, CH2Cl2/MeOH/heptane, 4:1:5) gave N-2-amino-4-(4-methyl-1-piperazinyl)-]-phenyl-8-quinolinesulfonamide (0.110 g , 35%). MS (posES-FIA) m/z=found: 384.2. calcd 383.48. %); Anal. (C19H22ClN5O2S.3H2O ) C, H, N, S and a small amount of the bis-sulfonylated N-{4-(4-methyl-1-piperazinyl)-2-[(8-quinolinylsulfonyl)amino]phenyl}-8-quinolinesulfonamide (0.070 g, 15%). The product was converted to HCl salt before analysis; MS (posES-FIA) m/z=found: 589.6. calcd: 588.16. Anal. (C29H29ClN6O4S2.2H2O) C, H, N.

Workup

  1. washAfter 1 h at room temperature the mixture was washed with aq NaHCO3 (10%)
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed
  4. customPurification by chromatography (SiO2, CH2Cl2/MeOH/heptane, 4:1:5)

Sources & evidence

ORD record
ord-b308b2acf2cb4ae095865f5f24117824
Source dataset
uspto-grants-2005_11
Patent number
US06969710B2

Reaction notes

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