Hydrochloric Acid → 3-Chloro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide-1-oxide

HRID 414037

Reaktionsgleichung

Reaktionsgleichung von HRID 414037
[Cl:1][C:2]1[C:3]([S:8]([NH2:11])(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:12](=O)([O:14]C1C=CC=CC=1)N.[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26]([NH2:32])[N:25]=1.C1CCN2C(=NCCC2)CC1.Cl.[OH2:45]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:45])[C:3]=1[S:8]([NH:11][C:12]([NH:32][C:26]1[N:27]=[C:28]([O:30][CH3:31])[CH:29]=[C:24]([O:23][CH3:22])[N:25]=1)=[O:14])(=[O:9])=[O:10]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 69322Phenyl carbamateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 146531913-Chloropyridine-2-sulfonamide

Produkt 1

HCID 146531933-Chloro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide-1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirring solution of the N-oxide of 3-chloro-2-pyridinesulfonamide (85 mg, 0.4 mmol) and the phenyl carbamate of 4,6-dimethoxy-2-aminopyrimidine (114 mg, 0.40 mmol) in acetonitrile was added DBU (62 mg, 0.40 mmol). Addition of H2O followed by 5% HCl caused a precipitate to form which was collected, m.p. 144°-147° C. NMR (200 MHz, d6 -DMSO) δ 3.91 (s, 6H), 5.998 (s, 1H), 7.7 (m, 2H), 8.4 (d, 1H), 10.8 (br s, 1H) and 13.1 (br s, 1H); IR (nujol) 1710 (s) cm-1 ; mass spectrum m/e 390 (M+, calc. for C12H12ClN5O6S 389+1).

Aufarbeitung

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Quellen und Nachweise

ORD-Eintrag
ord-99f0a07897394466824deb4e90cc583d
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04789465

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