Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (R)-N-[1-(2,4-Difluorophenyl)-ethyl]-4-iodo-2-(quinoxaline-5-sulfonylamino)-benzamide

HRID 551999Notes

Reaction equation

HRID 551999 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.Cl.[F:50][C:51]1[CH:56]=[C:55]([F:57])[CH:54]=[CH:53][C:52]=1[C@H:58]([NH2:60])[CH3:59]>>[F:50][C:51]1[CH:56]=[C:55]([F:57])[CH:54]=[CH:53][C:52]=1[C@H:58]([NH:60][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([I:25])=[CH:27][C:28]=1[NH:35][S:36]([C:39]1[C:40]2[N:41]=[CH:42][CH:43]=[N:44][C:45]=2[CH:46]=[CH:47][CH:48]=1)(=[O:38])=[O:37])[CH3:59]

Participants

4

Reactant 3

HCID 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 acidHCID 44828513(1R)-1-(2,4-difluorophenyl)ethan-1-amine hydrochloride

Product 1

HCID 11456125(R)-N-[1-(2,4-Difluorophenyl)-ethyl]-4-iodo-2-(quinoxaline-5-sulfonylamino)-benzamide

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)-1-(2,4-difluorophenyl)ethylamine hydrochloride (EXAMPLE 2, Method 1, Step C) and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C23H17F2IN4O3S, 594.0; m/z found, 593 [M−H]−. HPLC (reverse phase): RT=10.16 min. 1H NMR (500 MHz, CDCl3): 11.22 (s, 1H), 8.84 (d, J=1.8 Hz, 1H), 8.79 (d, J=1.8 Hz, 1H), 8.55 (dd, J=7.4, 1.4 Hz, 1H), 8.30 (dd, J=7.4, 1.4 Hz, 1H), 8.11 (d, J=1.8 Hz, 1H), 7.87 (dd, J=8.4, 7.4 Hz, 1H), 7.32-7.27 (m, 2H), 6.99 (d, J=8.2, 1H), 6.89-6.85 (m, 1H), 6.85-6.80 (m, 1H), 6.33 (br d, J=7.7 Hz, 1H), 5.35-5.27 (m, 1H), 1.53 (d, J=7.0 Hz, 3H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-cabfd0a12da44bae97349e4822970d09
Source dataset
uspto-grants-2011_05
Patent number
US07947833B2

Reaction notes

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