Morpholine → 4-[4-Iodo-2-[(5-quinoxalinylsulfonyl)amino]benzoyl]-morpholine

HRID 230051Notes

Reaction equation

HRID 230051 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.[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>>[I:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)=[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 8083MorpholineHCID 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 113529714-[4-Iodo-2-[(5-quinoxalinylsulfonyl)amino]benzoyl]-morpholine

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 morpholine and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C19H17IN4O4S, 524.0; m/z found, 523 [M−H]−. HPLC (reverse phase): RT=8.32 min. 1H NMR (500 MHz, CDCl3, rotameric broadening): 9.06 (d, J=1.8 Hz, 1H), 9.02 (d, J=1.8 Hz, 1H), 9.01 (br s, 1H), 8.51 (dd, J=7.0, 1.5 Hz, 1H), 8.37 (dd, J=8.4, 1.4 Hz, 1H), 7.96 (d, J=1.5 Hz, 1H), 7.90 (dd, J=8.4, 7.4 Hz, 1H), 7.38 (dd, J=8.0, 1.6 Hz, 1H), 6.76 (d, J=8.0 Hz, 1H), 3.70-3.40 (br m, 6H), 3.30-3.05 (br m, 2H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-5cc3bc17374f4e6a8f446a072c4fff43
Source dataset
uspto-grants-2009_07
Patent number
US07563895B2

Reaction notes

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