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

HRID 1464381Notes

Reaction equation

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

Participants

Reactant 4

HCID 218852-Dimethylaminopyridine

HCID 72879Methanesulfonamide

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

HCID 190877852-[3-Bromo-4-(quinolin-2-yl-methoxy)phenyl]acetic acid

Product 1

HCID 190877782-[3-Bromo-4-(quinolin-2-yl-methoxy)phenyl]acetylmethanesulphonamide

Procedure

In anology to the procedure of Example XVI, the title compound is prepared from 2.8 g (7.5 mmol) of the compound from Example XXI, 0.71 g (7.5 mmol) of dried methanesulphonamide, 1.44 g (7.5 mmol) of N-ethyl-N'-dimethylaminopropylcarbodiimide hydrochloride and 0.92 g (7.5 mmol) of dimethylaminopyridine.

Sources & evidence

ORD record: ord-c862680919a641f0b40daec025283d28
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05304563

Reaction notes

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