(R)-3-Methylmorpholine → (r)-Quinoxaline-5-sulfonic acid [5-iodo-2-(3-methylmorpholine-4-carbonyl)-phenyl]-amide

HRID 230059Notes

Reaction equation

HRID 230059 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[I: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>>[I: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

Participants

4

Reactant 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 160907584-Iodo-2-(quinoxaline-5-sulfonylamino)benzoic acid

Product 1

HCID 11478219(r)-Quinoxaline-5-sulfonic acid [5-iodo-2-(3-methylmorpholine-4-carbonyl)-phenyl]-amide

Procedure

The title compound was prepared from the HATU-mediated coupling of 4-iodo-2-(quinoxaline-5-sulfonylamino)benzoic acid (EXAMPLE 4, Step D) and (R)-3-methylmorpholine and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C20H19IN4O4S, 538.0; m/z found, 537 [M−H]−. HPLC (reverse phase): RT=8.71 min. 1H NMR (400 MHz, CDCl3, rotameric broadening): 9.05 (d, J=1.8 Hz, 1H), 9.00 (d, J=1.8 Hz, 1H), 8.94 (br s, 1H), 8.54 (dd, J=7.0, 1.5 Hz, 1H), 8.37 (dd, J=8.4, 1.4 Hz, 1H), 7.92 (dd, J=8.4, 7.4 Hz, 1H), 7.90-7.89 (m, 1H), 7.37 (dd, J=8.0, 1.6 Hz, 1H), 6.78 (d, J=8.0 Hz, 1H), 4.5-4.0 (br m, 1H), 3.90-3.82 (m, 1H), 3.66-3.64 (m, 1H), 3.47 (dd, J=11.5, 2.7 Hz, 1H), 3.35-3.25 (m, 3H), 1.31-1.21 (br m, 3H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-1c2e69e75b5642a9a9592dde5dd771fb
Source dataset
uspto-grants-2009_07
Patent number
US07563895B2

Reaction notes

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