Triethylamine → N-(2-t-Butoxycarbonylaminophenyl)-4-[3-(4-methylpiperazin-1-yl)propylaminomethyl]benzamide

HRID 658032Notes

Reaction equation

HRID 658032 reaction equation
CS(Cl)(=O)=O.[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([CH2:28]O)=[CH:24][CH:23]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.[NH2:38][CH2:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]1>ClCCl.O>[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:30])[C:22]1[CH:23]=[CH:24][C:25]([CH2:28][NH:38][CH2:39][CH2:40][CH2:41][N:42]2[CH2:43][CH2:44][N:45]([CH3:48])[CH2:46][CH2:47]2)=[CH:26][CH:27]=1)=[O:12])([CH3:8])([CH3:7])[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 20786191N-(2-t-Butoxycarbonylaminophenyl)-4-hydroxymethylbenzamide

Product 1

HCID 58001232N-(2-t-Butoxycarbonylaminophenyl)-4-[3-(4-methylpiperazin-1-yl)propylaminomethyl]benzamideYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, methanesulfonyl chloride (0.25 mL, 3.2 mmol) was added to a solution of N-(2-t-butoxycarbonylaminophenyl)-4-hydroxymethylbenzamide (Reference Compound No. 3-1, 1.0 g, 2.9 mmol) and triethylamine (0.61 mL, 4.4 mmol) in anhydrous dichloromethane (15 mL), and then the mixture was stirred for 40 minutes. 1-(3-Aminopropyl)-4-methylpiperazine (2.3 mL, 4.4 mmol) was added to the reaction mixture, and then stirred at room temperature for 2.5 hours additionally. Water (200 mL) was added thereto, the whole was extracted with ethyl acetate (200 mL) twice, and then the organic layer was washed with brine (200 mL). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH-modified silica gel, chloroform-methanol) to give 470 mg of the title reference compound as a colorless amorphous product. (Yield 33%)

Workup

  1. stirringstirred at room temperature for 2.5 hours additionally
  2. extractionthe whole was extracted with ethyl acetate (200 mL) twice
  3. washthe organic layer was washed with brine (200 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH-modified silica gel, chloroform-methanol)
  7. customto give 470 mg of the title reference compound as a colorless amorphous product

Sources & evidence

ORD record
ord-36636d040c494b39a7b49ff8cb9f5336
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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