Azepane → Quinoxaline-5-sulfonic acid [2-(azepane-1-carbonyl)-5-bromophenyl]-amide

HRID 230061Notes

Reaction equation

HRID 230061 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.[NH:49]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>>[N:49]1([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])[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

4

Reactant 3

HCID 8119AzepaneHCID 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 11752167Quinoxaline-5-sulfonic acid [2-(azepane-1-carbonyl)-5-bromophenyl]-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 azepane and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C21H21BrN4O3S, 488.0; m/z found, 487/489 [M−H]−. HPLC (reverse phase): RT=9.34 min. 1H NMR (500 MHz, CDCl3, rotameric broadening): 9.08 (d, J=1.8 Hz, 1H), 9.00 (d, J=1.8 Hz, 1H), 8.87 (br s, 1H), 8.50 (d, J=7.3 Hz, 1H), 8.34 (d, J=8.4 Hz, 1H), 7.87 (dd, J=8.4, 7.4 Hz, 1H), 7.80 (d, J=1.8 Hz, 1H), 7.16 (dd, J=8.1, 1.8 Hz, 1H), 6.91 (d, J=8.1 Hz, 1H), 3.33-3.28 (br m, 2H), 2.93-2.91 (m, 2H), 1.68-1.65 (m, 2H), 1.58-1.52 (m, 2H), 1.50-1.42 (br m, 4H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-161294cf4e9a43e781165766e9afe6d0
Source dataset
uspto-grants-2009_07
Patent number
US07563895B2

Reaction notes

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