2-Dimethylaminopyridine → N-[3-Ethyl-4-(quinolin-2-yl-methoxy)phenyl]acetylmethanesulphonamide

HRID 1464394Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:21][C:22]([OH:24])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH3:2].[CH3:25][S:26]([NH2:29])(=[O:28])=[O:27].Cl.CN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C>>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:21][C:22]([NH:29][S:26]([CH3:25])(=[O:28])=[O:27])=[O:24])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH3:2]

Participants

Reactant 4

HCID 218852-Dimethylaminopyridine

HCID 72879Methanesulfonamide

HCID 190877752-[3-Ethyl-4-(quinolin-2-yl-methoxy)phenyl]acetic acid

HCID 196086511-(3-Dimethylaminopropyl)-3-methylcarbodiimide hydrochloride

Product 1

HCID 19087800N-[3-Ethyl-4-(quinolin-2-yl-methoxy)phenyl]acetylmethanesulphonamide

Procedure

Analogously to the procedure of Example XVI, the title compound is prepared from 1.7 g (5.3 mmol) of the compound from Example XXXV, 0.6 g (6 mmol) of methanesulphonamide, 1.2 g (6 mmol) of N-methyl-N'-dimethylaminopropylcarbodiimide hydrochloride and 0.8 g (6 mmol) of dimethylaminopyridine.

Sources & evidence

ORD record: ord-e07d37890a13443bbf4aa7f45a6f0de2
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05304563

Reaction notes

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