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

반응식

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.[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]([I: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

참가 물질

반응물 3

HCID 8119Azepane

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 acid

생성물 1

HCID 11444027Quinoxaline-5-sulfonic acid [2-(azepane-1-carbonyl)-5-iodophenyl]-amide

실험 절차

The title compound was prepared from the HATU-mediated coupling of 4-iodo-2-(quinoxaline-5-sulfonylamino)benzoic acid (EXAMPLE 4, Step D) and azepane and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C21H21IN4O3S, 536.0; m/z found, 535 [M−H]−. HPLC (reverse phase): RT=9.42 min. 1H NMR (500 MHz, CDCl3, rotameric broadening): 9.08 (d, J=1.8 Hz, 1H), 9.00 (d, J=1.8 Hz, 1H), 8.81 (br s, 1H), 8.49 (d, J=7.3, 1H), 8.35 (d, J=8.4, Hz, 1H), 7.98 (s, 1H), 7.88 (t, J=8.1 Hz, 1H), 7.37 (d, J=8.1 Hz, 1H), 6.75 (d, J=8.0 Hz, 1H), 3.30-3.27 (br m, 2H), 2.91-2.89 (m, 2H), 1.66-1.63 (m, 2H), 1.63-1.54 (m, 2H), 1.50-1.43 (br m, 4H).