Dichloromethane → HCID 22660821, Verbindung

HRID 392977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392977
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:25]3[CH:33]=[CH:34][C:35]([C:37](O)=[O:38])=[CH:36][C:24]=3[N:23]=2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClCCl>CN(C)C=O>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:26]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[C:25]3[CH:33]=[CH:34][C:35]([C:37]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:38])=[CH:36][C:24]=3[N:23]=2)=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 491098HCID 491098, Verbindung

Produkt 1

HCID 22660821HCID 22660821, VerbindungAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methanesulfonamide (0.0188 g, 0.198 mmol), sodium hydride, and the acid chloride of 49 (0.0083 g, 0.019 mmol) were reacted in dimethylformamide and dichloromethane according to the procedure described for example 8. The crude material was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid) to afford the product as a white solid (0.0055 g, 52%). 1H NMR (CDCl3) δ 8.68 (s, 1H), 8.17 (d, 1H, J=8.8 Hz), 7.91 (d, 1H, J=8.8 Hz), 7.69 (d, 2H, J=8.5 Hz), 7.48-7.37 (m, 5H), 7.24 (d, 2H, J=8.7 Hz), 5.18 (s, 2H), 4.57 (m, 1H), 3.34 (s, 3H), 2.34 (br m, 2H), 2.06 (br m, 4H), 1.85 (br m, 1H), 1.39 (br m, 3H); ESI-MS m/e 504.3 (M+1); HPLC purity (ELSD)>95%.

Aufarbeitung

  1. customThe crude material was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-5fb3c26bd4f147d6aaa9eb9be99ef7e0
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803374B2

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