4-Chlorobenzenesulfonyl chloride → [5-(4-Chloro-benzenesulfonylamino)-pentyl]-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

HRID 882898Notes

Reaction equation

HRID 882898 reaction equation
[Br-:1].[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N+:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15])([CH3:10])[CH3:9].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.CN1CCOCC1>CN(C=O)C.CO.C(Cl)Cl>[Br-:1].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N+:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=2)=[O:15])([CH3:9])[CH3:10])(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 86656644(5-Amino-pentyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide2×

Product 1

HCID 57391529[5-(4-Chloro-benzenesulfonylamino)-pentyl]-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-amino-pentyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate O) (0.25 g, 0.59 mmol), 4-chlorobenzenesulfonyl chloride (0.13 g, 0.59 mmol) and N-methylmorpholine (0.30 mL, 2.73 mmol) in DMF (5 mL) is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and is purified by column chromatography (basic alumina, 0-10% MeOH in DCM). The solid that is obtained is dissolved in a minimum amount of MeOH and DCM then precipitated by the addition of diethyl ether. The supernatant solvent mixture is decanted and the product is washed again with diethyl ether then dried under vacuum to give the title compound. M+ 578. 1H NMR (400 MHz, DMSO-d6) δ 8.25 (1H, t), 7.78 (2H, d), 7.74 (1H, t), 7.57 (2H, br), 7.67 (2H, d), 7.11 (2H, br), 3.56 (2H, q), 3.36 (2H, t), 3.28-3.22 (2H, m), 3.04 (6H, s), 2.95 (2H, q), 1.65-1.58 (2H, m), 1.37 (2H, quintet), 1.24-1.16 (2H, m).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customis purified by column chromatography (basic alumina, 0-10% MeOH in DCM)
  3. customThe solid that is obtained
  4. customthen precipitated by the addition of diethyl ether
  5. customThe supernatant solvent mixture is decanted
  6. washthe product is washed again with diethyl ether
  7. customthen dried under vacuum

Sources & evidence

ORD record
ord-c40a8b86520c4addabf2e0bbd007d7db
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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