N-[[18-[2-[4-(isopropyl)thiazol-2-yl]-7-methoxyquinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-4-yl]carbonyl](cyclopropyl)sulfonamide → N-[18-[8-bromo-2-(thiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carbonyl]-(cyclopropyl)sulfonamide

HRID 1669565Notes

Reaction equation

HRID 1669565 reaction equation
[Br:1][C:2]1[C:3]([O:42][CH3:43])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[CH:15][N:16]=1)[CH:8]=[C:7]2[O:17][CH:18]1[CH2:36][CH:35]2[N:20]([C:21](=[O:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH:30]3[C:32]([C:38]([OH:40])=O)([NH:33][C:34]2=[O:37])[CH2:31]3)[CH2:19]1.C(C1N=C(C2C=C(OC3CC4N(C(=O)CCCCCCC=CC5C(C([NH:85][S:86]([CH:89]6[CH2:91][CH2:90]6)(=[O:88])=[O:87])=O)(NC4=O)C5)C3)C3C(=CC(OC)=CC=3)N=2)SC=1)(C)C>>[Br:1][C:2]1[C:3]([O:42][CH3:43])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[CH:15][N:16]=1)[CH:8]=[C:7]2[O:17][CH:18]1[CH2:36][CH:35]2[N:20]([C:21](=[O:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH:30]3[C:32]([C:38]([NH:85][S:86]([CH:89]4[CH2:91][CH2:90]4)(=[O:88])=[O:87])=[O:40])([NH:33][C:34]2=[O:37])[CH2:31]3)[CH2:19]1

Participants

3

Reactant 2

HCID 67318810N-[[18-[2-[4-(isopropyl)thiazol-2-yl]-7-methoxyquinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-4-yl]carbonyl](cyclopropyl)sulfonamideHCID 6731931618-[8-Bromo-7-methoxy-2-(thiazol-2-yl)quinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid

Product 1

HCID 67319968N-[18-[8-bromo-2-(thiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carbonyl]-(cyclopropyl)sulfonamide

Procedure

The title compound was prepared from 18-[8-bromo-7-methoxy-2-(thiazol-2-yl)-quinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid (41) following the procedure reported for synthesis of N-[[18-[2-[4-(isopropyl)thiazol-2-yl]-7-methoxyquinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]nonadec-7-en-4-yl]carbonyl](cyclopropyl)sulfonamide 11: m/z=773 (M+H)+. 1H NMR (CDCl3): 0.90-0.98 (m, 1H), 1.05-2.0 (m, 2H), 1.27-1.58 (m, 9H), 1.80-1.97 (m, 3H), 2.18-2.24 (m, 1H), 2.29-2.38 (m, 1H), 2.48-2.62 (m, 2H), 2.69-2.73 (m, 2H), 2.88-2.94 (m, 1H), 4.01 (d, J=11.8 Hz, 1H), 4.08 (s, 3H), 4.12 (dd, J=11.5 Hz, J=3.6 Hz, 1H), 4.61 (t, J=7.9 Hz, 1H), 5.00 (t, J=9.5 Hz, 1H), 5.47-5.60 (m, 1H), 5.70-5.77 (m, 1H), 6.69 (br s, 1H), 7.24 (d, J=9.2 Hz, 1H), 7.55 (d, J=3.2 Hz, 1H), 7.59 (s, 1H), 7.98 (d, J=3.2 Hz, 1H), 8.05 (d, J=9.2 Hz, 1H), 8.20 (br s, 1H).

Sources & evidence

ORD record
ord-a7f5a3539735401fa012a345bc6519c4
Source dataset
uspto-grants-2011_08
Patent number
US07989471B2

Reaction notes

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