Methanesulfonyl chloride → N-Ethyl-N-(6-methanesulphonamidoquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine hydrochloride

HRID 345026Notes

Reaction equation

HRID 345026 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[CH2:6]([N:8]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:25][CH:24]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:20])[CH:16]=2)[N:11]=1)[CH3:7]>N1C=CC=CC=1>[ClH:5].[CH2:6]([N:8]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH3:33])(=[O:31])=[O:32])=[CH:25][CH:24]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:20][S:2]([CH3:1])(=[O:4])=[O:3])[CH:16]=2)[N:11]=1)[CH3:7]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19813422N-ethyl-N-(6-aminoquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine

Product 1

HCID 19813440N-Ethyl-N-(6-methanesulphonamidoquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.1 g, 1.29 mmole) was reacted with N-ethyl-N-(6-aminoquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine (see Preparation 11B - 0.51 g, 1.23 mmole) in pyridine similarly to the procedure of Example 2, giving the free base of the title compound as a gum. The gum was dissolved in ethyl acetate and the solution was diluted with ethereal hydrogen chloride and evaporated to dryness. The residue was triturated with ether to give the title compound as a foam, yield 0.06 g, m.p. 96°.

Sources & evidence

ORD record
ord-848b0ac6718a40379e42ee16b4c042e4
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

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