1-Hydroxybenzotriazole → N-(12-mesyloxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003297Notes

Reaction equation

HRID 1003297 reaction equation
Cl.[CH3:2][S:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])(=[O:5])=[O:4].[CH2:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[N:33]=[CH:32][C:31]([C:34]([O-])=[O:35])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)[CH3:21].[Na+].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.C(Cl)(Cl)Cl>[S:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:34]([C:31]1[CH:32]=[N:33][C:28]([N:25]2[CH2:24][CH2:23][N:22]([CH2:20][CH3:21])[CH2:27][CH2:26]2)=[CH:29][CH:30]=1)=[O:35])([CH3:2])(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1879641312-Aminododecyl methanesulfonate hydrochlorideHCID 23663821Sodium 6-(4-ethylpiperazinyl)pyridine-3-carboxylate

Product 1

HCID 15462632N-(12-mesyloxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamideYield 83.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.77 g of 12-aminododecyl methanesulfonate hydrochloride in 100 ml of methylene chloride were added successively under ice-cooling 3.60 g of sodium 6-(4-ethyl-1-piperazinyl)pyridine-3-carboxylate, 2.89 g of 1-hydroxybenzotriazole (HOBt), 1.99 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCI) and then the mixture was stirred overnight. The reaction solution was diluted with chloroform and washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then distilled under reduced pressure. The residue thus obtained was chromatographed over a silica gel column to afford 4.96 g of the title compound.

Workup

  1. washwashed successively with water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customThe residue thus obtained
  5. customwas chromatographed over a silica gel column

Sources & evidence

ORD record
ord-25d5fc165638468093e8c129caab0f65
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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