(R)-3-Methylmorpholine → (R)-4-[4-chloro-2-[(5-quinoxalinylsulfonyl)amino]benzoyl]-3-methylmorpholine

HRID 230054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230054
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl: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.[CH3:49][C@@H:50]1[CH2:55][O:54][CH2:53][CH2:52][NH:51]1>>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([N:51]2[CH2:52][CH2:53][O:54][CH2:55][C@H:50]2[CH3:49])=[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 641498(R)-3-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid

Produkt 1

HCID 11293780(R)-4-[4-chloro-2-[(5-quinoxalinylsulfonyl)amino]benzoyl]-3-methylmorpholine

Versuchsvorschrift

The title compound was prepared from the HATU-mediated coupling of 4-chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid (EXAMPLE 3, Step B) and (R)-3-methylmorpholine (EXAMPLE 12, Step B) and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C20H19ClN4O4S, 446.1; m/z found, 445 [M−H]−. HPLC (reverse phase): RT=8.54 min. 1H NMR (500 MHz, CDCl3, rotameric broadening): 9.05 (d, J=1.8 Hz, 1H), 9.04 (br s, 1H), 9.00 (d, J=1.8 Hz, 1H), 8.56 (dd, J=7.0, 1.5 Hz, 1H), 8.37 (dd, J=8.4, 1.4 Hz, 1H), 7.91 (dd, J=8.4, 7.4 Hz, 1H), 7.56 (br s, 1H), 7.01-6.98 (m, 2H), 4.4-4.2 (br m, 1H), 3.90-3.82 (m, 1H), 3.68-3.62 (m, 1H), 3.51 (dd, J=11.5, 2.7 Hz, 1H), 3.40-3.20 (m, 3H), 1.31-1.23 (br m, 3H).

Aufarbeitung

  1. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-2b8ecf3d760740d180b982a26ec6ad64
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563895B2

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