Sodium Hydroxide → 5-Chloro-2-methoxy-N-(2-(1-(3-propylureidosulfonyl)piperidin-4-yl)ethyl)benzamide

HRID 2043080Notes

Reaction equation

HRID 2043080 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8].[OH-].[Na+].[CH2:27]([NH:30][C:31](=[O:36])C(Cl)(Cl)Cl)[CH2:28][CH3:29]>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH:21][C:31]([NH:30][CH2:27][CH2:28][CH3:29])=[O:36])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4287575N-(n-propyl)trichloroacetamideHCID 122820304-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide

Product 1

HCID 122818885-Chloro-2-methoxy-N-(2-(1-(3-propylureidosulfonyl)piperidin-4-yl)ethyl)benzamideYield 14.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

376 mg (1 mmol) of 4-(2-(5-chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide and 160 mg (4 mmol) of sodium hydroxide were heated in 5 ml of N-methyl-2-pyrrolidone with 410 mg (2 mmol) of N-(n-propyl)trichloroacetamide at 80° C. for 10 minutes. The reaction mixture was poured onto ice/2 M hydrochloric acid, and the precipitated solid was filtered off with suction and washed with water until neutral. Purification by chromatography (silica gel; toluene/ethanol/ethyl acetate 8/1/1) resulted in 65 mg (14%) of the title compound as a colorless solid.

Workup

  1. additionThe reaction mixture was poured onto ice/2 M hydrochloric acid
  2. filtrationthe precipitated solid was filtered off with suction
  3. washwashed with water until neutral
  4. customPurification by chromatography (silica gel; toluene/ethanol/ethyl acetate 8/1/1)

Sources & evidence

ORD record
ord-1e069954c82d4a7ea8c7087749d4f11c
Source dataset
uspto-grants-2013_11
Patent number
US08586612B2

Reaction notes

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