Triethylamine → Methyl 4-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-1-methyl-4-piperidinecarboxylate

HRID 2289824Notes

Reaction equation

HRID 2289824 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12](Cl)(=[O:14])=[O:13])[CH:10]=2)[C:5]([Cl:16])=[CH:4][N:3]=1.[NH2:17][C:18]1([C:25]([O:27][CH3:28])=[O:26])[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1.C(N(CC)CC)C>C(Cl)Cl>[NH3:3].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([NH:17][C:18]3([C:25]([O:27][CH3:28])=[O:26])[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]3)(=[O:14])=[O:13])[CH:10]=2)[C:5]([Cl:16])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chlorideHCID 18698416Methyl 4-amino-1-methylpiperidine-4-carboxylate

Product 2

HCID 222AmmoniaHCID 16658106Methyl 4-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-1-methyl-4-piperidinecarboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,4-Dichloro-7-isoquinolinylsulphonyl chloride (1.0 g, 3.37 mmol) was added to a solution of methyl 4-amino-1-methyl-4-piperidinecarboxylate (700 mg, 4.0 mmol) and triethylamine (700 μl, 1.0 mmol) in CH2Cl2 (60 ml), and the reaction stirred at room temperature for 18 h. The mixture was concentrated in vacuo, and the residue purified by column chromatography upon silica gel using an elution gradient of CH2Cl2 -MeOH-0.880 NH3 (97:3:0.3 to 95:5:0.5) to give methyl 4-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-1-methyl-4-piperidinecarboxylate (700 mg, 1.62 mmol) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by column chromatography upon silica gel using an elution gradient of CH2Cl2 -MeOH-0

Sources & evidence

ORD record
ord-fa52b94077394710948d90e4f67cab95
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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