2-Chloro-4-fluorobenzylamine → 4-Bromo-N-(2-chloro-4-fluoro-benzyl)-2-(quinoxaline-5-sulfonylamino)-benzamide

HRID 552000

Reaktionsgleichung

Reaktionsgleichung von HRID 552000
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[C:28]([NH:35][S:36]([C:39]2[C:40]3[N:41]=[CH:42][CH:43]=[N:44][C:45]=3[CH:46]=[CH:47][CH:48]=2)(=[O:38])=[O:37])[CH:27]=1.[Cl:49][C:50]1[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:51]=1[CH2:52][NH2:53]>>[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:53][CH2:52][C:51]2[CH:54]=[CH:55][C:56]([F:58])=[CH:57][C:50]=2[Cl:49])=[O:31])=[C:28]([NH:35][S:36]([C:39]2[C:40]3[N:41]=[CH:42][CH:43]=[N:44][C:45]=3[CH:46]=[CH:47][CH:48]=2)(=[O:38])=[O:37])[CH:27]=1

Komponenten

4

Edukt 3

HCID 1399092-Chloro-4-fluorobenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114297084-Bromo-2-(quinoxaline-5-sulfonylamino)benzoic acid

Produkt 1

HCID 113987334-Bromo-N-(2-chloro-4-fluoro-benzyl)-2-(quinoxaline-5-sulfonylamino)-benzamide

Versuchsvorschrift

The title compound was prepared from the HATU-mediated coupling of 4-bromo-2-(quinoxaline-5-sulfonylamino)benzoic acid (EXAMPLE 1, Step G) and 2-chloro-4-fluorobenzylamine and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C22H15BrClFN4O3S, 548.0; m/z found, 549/550 [M+H]+, 571/573 [M+Na]+. HPLC (reverse phase): RT=9.86 min. 1H NMR (500 MHz, CDCl3): 11.29 (s, 1H), 8.88 (dd, J=15.3, 6.0 Hz, 2H), 8.57 (dd, J=7.4, 1.4 Hz, 1H), 8.32 (dd, J=8.4, 1.8 Hz, 1H), 8.31 (d, J=1.8 Hz, 1H), 7.93 (d, J=1.8 Hz, 1H), 7.88 (dd, J=8.4, 7.4 Hz, 1H), 7.43 (dd, J=8.5, 6.0 Hz, 1H), 7.16 (dd, J=8.3, 2.6, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.07 (dd, J=8.5, 2.1 Hz, 1H), 7.01 (ddd, J=8.2, 8.2, 2.5 Hz, 1H), 6.38-6.33 (m, 1H), 4.57 (d, J=6.0 Hz, 1H).

Aufarbeitung

  1. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-7ade52816b994ec4bbeca64743f7d2cf
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947833B2

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