Diisopropylethylamine → 4-[4-Amino-5-(3-fluoro-4-methoxybenzoyl)thiazol-2-ylamino]piperidine-1-sulfonic acid dimethylamide

HRID 30159

Reaktionsgleichung

Reaktionsgleichung von HRID 30159
[NH2:1][C:2]1[N:3]=[C:4]([NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[S:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([F:17])[CH:10]=1)=[O:8].[CH3:25][N:26]([CH3:31])[S:27](Cl)(=[O:29])=[O:28].C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[CH3:25][N:26]([CH3:31])[S:27]([N:22]1[CH2:23][CH2:24][CH:19]([NH:18][C:4]2[S:5][C:6]([C:7](=[O:8])[C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([F:17])[CH:10]=3)=[C:2]([NH2:1])[N:3]=2)[CH2:20][CH2:21]1)(=[O:29])=[O:28]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 11951612[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone

Produkt 1

HCID 119517954-[4-Amino-5-(3-fluoro-4-methoxybenzoyl)thiazol-2-ylamino]piperidine-1-sulfonic acid dimethylamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluoro-4-methoxy-phenyl)methanone (0.08 g, 0.022 mmol) (Example 7)) was treated with dimethylsulfamoyl chloride in a manner similar to Example 9 except that diisopropylethylamine was additionally used as a catalyst and short plug of silica gel (ethyl acetate was used to pre-purify the sample to give 30 mg (22% yield) of 4-[4-amino-5-(3-fluoro-4-methoxybenzoyl)thiazol-2-ylamino]piperidine-1-sulfonic acid dimethylamide. 1H NMR (DMSO−d6, 300 MHz) δ1.51 (m, 2H, CH2), 1.97 (m, 2H, CH2), 2.77 (s, 6H, 2× NCH2), 2.99 (m, 2H, CH2), 3.52 (m, 2H, CH2), 3.6-4.0 (broad, 1H, CH), 3.89 (s, 3H, OCH3), 7.9-8.5 (brd, 2H, 2NH), 8.71 (brd, 1H, NH). HRMS: (M+H)+: observed: 458.1331; calcd for 4581327.

Aufarbeitung

  1. customto pre-purify the sample

Quellen und Nachweise

ORD-Eintrag
ord-e7096d1d9d8943dda7aeb1fa0b515d97
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423053B2

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