Piperidin-4-ol → Quinoxaline-5-sulfonic acid [2-(4-hydroxy-piperidine-1-carbonyl)-5-bromo-phenyl]-amide

HRID 230065Notes

Reaction equation

HRID 230065 reaction equation
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.[OH:49][CH:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>>[OH:49][CH:50]1[CH2:55][CH2:54][N:53]([C:30]([C:29]2[CH:33]=[CH:34][C:26]([Br:25])=[CH:27][C:28]=2[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])=[O:31])[CH2:52][CH2:51]1

Participants

4

Reactant 3

HCID 79341Piperidin-4-olHCID 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

Product 1

HCID 11306408Quinoxaline-5-sulfonic acid [2-(4-hydroxy-piperidine-1-carbonyl)-5-bromo-phenyl]-amide

Procedure

The title compound was prepared from the HATU-mediated coupling of 4-bromo-2-(quinoxaline-5-sulfonylamino)benzoic acid (EXAMPLE 1, Step G) and 4-hydroxypiperidine and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C20H19BrN4O4S, 490.0; m/z found, 491/493 [M+H]+, 513/515 [M+Na]+. HPLC (reverse phase): RT=7.68 min. 1H NMR (400 MHz, CDCl3, rotameric broadening): 9.08 (d, J=1.8 Hz, 1H), 9.02 (d, J=1.8 Hz, 1H), 8.95 (br s, 1H), 8.52-8.50 (m, 1H), 8.38-8.36 (m, 1H), 7.92-7.88 (m, 1H), 7.75 (d, J=1.6 Hz, 0.7H), 7.68 (d, J=1.6 Hz, 0.3H), 7.20-7.17 (m, 1H), 6.96-6.92 (m, 1H), 3.96-3.91 (m, 1H), 3.85-3.75 (m, 1H), 3.2-2.8 (m, 3H), 2.05-1.95 (m, 2H), 1.7-1.3 (m, 3H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-9145159bf70f41cc8f786d25f4ba78bb
Source dataset
uspto-grants-2009_07
Patent number
US07563895B2

Reaction notes

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