Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (S)-4-Chloro-N-[1-(2,4-difluoro-phenyl)-2,2,2-trifluoroethyl]-2-(quinoxaline-5-sulfonylamino)-benzamide

HRID 1182554Notes

Reaction equation

HRID 1182554 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl: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]([NH2:63])[C:59]([F:62])([F:61])[F:60]>>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:63][C@@H:58]([C:52]2[CH:53]=[CH:54][C:55]([F:57])=[CH:56][C:51]=2[F:50])[C:59]([F:60])([F:62])[F:61])=[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:37])=[O:38])[CH:27]=1

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 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acidHCID 86596675(S)-1-(2,4-difluorophenyl)-2,2,2-trifluoroethylamine hydrochloride

Product 1

HCID 11272921(S)-4-Chloro-N-[1-(2,4-difluoro-phenyl)-2,2,2-trifluoroethyl]-2-(quinoxaline-5-sulfonylamino)-benzamide

Procedure

(S)-4-Chloro-N-[1-(2,4-difluorophenyl)-2,2,2-trifluoroethyl-1]-2-(quinoxaline-5-sulfonylamino)-benzamide. The title compound was prepared from the HATU-mediated coupling of 4-chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid (EXAMPLE 3, Step B) and (S)-1-(2,4-difluorophenyl)-2,2,2-trifluoroethylamine hydrochloride and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C23H14ClF5N4O3S, 556.0; m/z found, 555/557 [M−H]−. HPLC (reverse phase): RT=9.98 min. 1H NMR (400 MHz, CDCl3): 11.07 (s, 1H), 8.84-8.83 (m, 2H), 8.56 (dd, J=7.4, 1.4 Hz, 1H), 8.31 (dd, J=7.4, 1.4 Hz, 1H), 7.87 (dd, J=8.4, 7.4 Hz, 1H), 7.81 (d, J=2.0 Hz, 1H), 7.43-7.37 (m, 1H), 7.30 (d, J=8.5 Hz, 1H), 7.03-6.93 (m, 3H), 6.81-6.79 (m, 1H), 6.08-6.00 (m, 1H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-a6d3ed0ce20a4366937c375df02ef61e
Source dataset
uspto-grants-2007_10
Patent number
US07288651B2

Reaction notes

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