2,4-Difluorobenzylamine → 4-Bromo-N-(2,4-difluoro-benzyl)-2-(quinoxaline-5-sulfonylamino)-benzamide

HRID 230057Notes

Reaction equation

HRID 230057 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.[F:49][C:50]1[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:51]=1[CH2:52][NH2:53]>>[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:53][CH2:52][C:51]2[CH:54]=[CH:55][C:56]([F:58])=[CH:57][C:50]=2[F: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 27332442,4-DifluorobenzylamineHCID 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 111685834-Bromo-N-(2,4-difluoro-benzyl)-2-(quinoxaline-5-sulfonylamino)-benzamide

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 2,4-difluorobenzylamine and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C22H15BrF2N4O3S, 532.0; m/z found, 533/535 [M+H]+, 555/557 [M+Na]+. HPLC (reverse phase): RT=9.64 min. 1H NMR (500 MHz, CDCl3, rotameric broadening): 11.31 (s, 1H), 8.92-8.86 (m, 2H), 8.62-8.53 (m, 1H), 8.35-8.29 (m, 1H), 7.96-7.90 (m, 1H), 7.90-7.83 (m, 1H), 7.41-7.32 (m, 1H), 7.15-7.10 (m, 1H), 7.09-7.03 (m, 1H), 6.94-6.82 (m, 2H), 6.31-6.24 (m, 1H), 4.53 (br s, 2H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-d3cfc98fb26442a0b91e7219511bd44d
Source dataset
uspto-grants-2009_07
Patent number
US07563895B2

Reaction notes

Loading…