Morpholine → Quinoxaline-5-sulfonic acid [4,5-dichloro-2-(morpholine-4-carbonyl)-phenyl]-amide

HRID 552004

Reaction equation

HRID 552004 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[C:34]([Cl:35])=[CH:33][C:29]([C:30]([OH:32])=O)=[C:28]([NH:36][S:37]([C:40]2[C:41]3[N:42]=[CH:43][CH:44]=[N:45][C:46]=3[CH:47]=[CH:48][CH:49]=2)(=[O:39])=[O:38])[CH:27]=1.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>>[Cl:35][C:34]1[C:26]([Cl:25])=[CH:27][C:28]([NH:36][S:37]([C:40]2[C:41]3[N:42]=[CH:43][CH:44]=[N:45][C:46]=3[CH:47]=[CH:48][CH:49]=2)(=[O:38])=[O:39])=[C:29]([C:30]([N:50]2[CH2:55][CH2:54][O:53][CH2:52][CH2:51]2)=[O:32])[CH:33]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 160907694,5-Dichloro-2-(quinoxaline-5-sulfonylamino)-benzoic acid

Product 1

HCID 11259878Quinoxaline-5-sulfonic acid [4,5-dichloro-2-(morpholine-4-carbonyl)-phenyl]-amide

Procedure

The title compound was prepared from the HATU-mediated coupling of 4,5-dichloro-2-(quinoxaline-5-sulfonylamino)-benzoic acid (EXAMPLE 5, Step D) and morpholine and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C19H16Cl2N4O4S, 466.0; m/z found, 465/467 [M−H]−. HPLC (reverse phase): RT=8.84 min. 1H NMR (500 MHz, CDCl3, rotameric broadening): 9.06 (d, J=1.8 Hz, 1H), 9.03 (d, J=1.8 Hz, 1H), 8.51 (dd, J=7.0, 1.5 Hz, 1H), 8.38 (dd, J=8.4, 1.4 Hz, 1H), 8.08 (d, J=1.5 Hz, 1H), 7.91 (dd, J=8.4, 7.4 Hz, 1H), 7.70 (s, 1H), 7.14 (s, 1H), 4.35-4.10 (br m, 4H), 3.65-3.48 (br m, 4H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-2e248425d42540a4a7835ccb219e4948
Source dataset
uspto-grants-2011_05
Patent number
US07947833B2

Linked notes

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