Pyridine → N-{4-(homopiperazinyl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride

HRID 2237676Notes

Reaction equation

HRID 2237676 reaction equation
[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C=CC(N2CCCN(C(OC(C)(C)C)=O)CC2)=CC=1N.N1C=CC=CC=1.[NH2:39][C:40]1[CH:45]=[C:44]([N:46]2[CH2:52][CH2:51][CH2:50][N:49](C(OC(C)(C)C)=O)[CH2:48][CH2:47]2)[CH:43]=[CH:42][C:41]=1[NH:60][S:61]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)(=[O:63])=[O:62].Cl.CCOCC>C(Cl)Cl.CO>[ClH:10].[N:46]1([C:44]2[CH:43]=[CH:42][C:41]([NH:60][S:61]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)(=[O:63])=[O:62])=[C:40]([NH:39][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:45]=2)[CH2:52][CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1

Participants

8

Reactant 5

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 10953452Ether hydrochlorideHCID 22272452N-{2-amino-4-[4-t-butyloxycarbonyl-homopiperazin-1-yl-]phenyl}benzenesulfonamideHCID 22272464Tert-butyl 4-(3,4-diaminophenyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 9828147N-{4-(homopiperazinyl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (0.088 g, 0.50 mmol) was added to a solution of 2-amino-5-(4-t-butyloxycarbonyl-homopiperazin-1-yl)aniline (0.153 g, 0.50 mmol) and pyridine (514 mL, 6.39 mmol) in DCM. After 1 h at r.t. the mixture was washed with NaHCO3 (10%) dried (MgSO4) and the solvent was removed. Purification by column chromatography (CH2Cl2/MeOH/heptane, 4:1:15) gave a mixture of N-{2-amino-4-[4-t-butyloxycarbonyl-homopiperazin-1-yl-]phenyl}benzenesulfonamide and of the bis-sulphonylated N-{4-[4-t-butyloxycarbonyl]homopiperazinyl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide (0.150 g, 86%). Boc-deprotection was achieved by dissolving the mixture in MeOH and adding HCl/ether. The mixture was let at r.t. for 0.5 h. Purification by preparative HPLC gave N-{4-(homopiperazinyl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride; Anal. (C23H27ClN4O4S2) C, H, N, S; M+ 487.4 Calcd 486.14. And N-{4-(homopiperazinyl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride; Anal. (C17H23ClN4O2S) C, H, N, S; M+ 347.5 Calcd 346.15.

Workup

  1. washAfter 1 h at r.t. the mixture was washed with NaHCO3 (10%)
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed
  4. customPurification by column chromatography (CH2Cl2/MeOH/heptane, 4:1:15)
  5. customgave
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-3aaf6afa364a4946bd0daed649e80dc6
Source dataset
uspto-grants-2010_05
Patent number
US07718650B2

Reaction notes

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