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Methyl chloroformate → methyl N-[4-[4-(6-chloronaphthalen-2-yl)sulfonylpiperazine-1-carbonyl]benzenecarboximidoyl]carbamate

HRID 278605
Notes
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Reaction equation

HRID 278605 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.C(N(CC)CC)C.Cl.[C:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)(=[NH:32])[NH2:31].Cl[C:43]([O:45][CH3:46])=[O:44]>ClCCl.CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([C:37](=[O:38])[C:36]3[CH:40]=[CH:41][C:33]([C:30](=[NH:32])[NH:31][C:43]([O:45][CH3:46])=[O:44])=[CH:34][CH:35]=3)[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 226280844-Amidinobenzoylchloride hydrochlorideHCID 227097661-(6-Chloronaphth-2-ylsulphonyl)piperazine hydrochloride

Product 1

HCID 145840733methyl N-[4-[4-(6-chloronaphthalen-2-yl)sulfonylpiperazine-1-carbonyl]benzenecarboximidoyl]carbamateYield 19.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (143 mg) and triethylamine (208 mg) in dichloromethane (10 ml) was added 4-amidinobenzoylchloride hydrochloride (108 mg), and the solution was stirred at room temperature for 1 hour, to which were added DMF (10 ml) and methyl chloroformate (200 mg). The solution was stirred at 50° C. for 30 minutes and the reaction solution was concentrated . The residue was dissolved in ethyl acetate, washed with water and sodium chloride solution, dried and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate/methanol=40:1) to give colorless crystals of the title compound (41 mg).

Workup

  1. stirringThe solution was stirred at 50° C. for 30 minutes
  2. concentrationthe reaction solution was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate/methanol=40:1)

Sources & evidence

ORD record
ord-534365849e7048628c5e463a043d2464
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06359134B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes