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-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-14,14-dimethyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carbonyl](cyclopropyl)sulfonamide

HRID 1669574Notes

Reaction equation

HRID 1669574 reaction equation
[Cl:1][C:2]1[C:3]([O:47][CH3:48])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][CH:21]1[CH2:39][CH:38]2[N:23]([C:24](=[O:46])[C:25]([CH3:45])([CH3:44])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=[CH:32][CH:33]3[C:35]([C:41]([OH:43])=O)([NH:36][C:37]2=[O:40])[CH2:34]3)[CH2:22]1.C(C1N=C(C2C=C(OC3CC4N(C(=O)CCCCCCC=CC5C(C([NH:90][S:91]([CH:94]6[CH2:96][CH2:95]6)(=[O:93])=[O:92])=O)(NC4=O)C5)C3)C3C(=CC(OC)=CC=3)N=2)SC=1)(C)C>>[Cl:1][C:2]1[C:3]([O:47][CH3:48])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][CH:21]1[CH2:39][CH:38]2[N:23]([C:24](=[O:46])[C:25]([CH3:45])([CH3:44])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=[CH:32][CH:33]3[C:35]([C:41]([NH:90][S:91]([CH:94]4[CH2:96][CH2:95]4)(=[O:93])=[O:92])=[O:43])([NH:36][C:37]2=[O:40])[CH2:34]3)[CH2:22]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 6732014618-[8-Chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-14,14-dimethyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid

Product 1

HCID 67319910N-[18-[8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-14,14-dimethyl-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-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-14,14-dimethyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid (54) 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=798 (M+H)+. 1H NMR (CDCl3): 0.96 (m, 1H), 1.05-1.15 (m, 2H), 1.17 (s, 3H), 1.32 (s, 3H), 1.23-1.36 (m, 7H), 1.38 (d, J=6.8 Hz, 6H), 1.43-1.53 (m, 2H), 1.75-1.94 (m, 3H), 2.39 (m, 1H), 2.56 (m, 3H), 2.85-2.95 (m, 1H), 3.20 (m, 1H), 4.02 (s, 3H), 4.15 (dd, J=3.7 Hz, J=11.6 Hz, 1H), 4.23 (d, J=11.6 Hz, 1H), 4.73 (t, J=7.5 Hz, 1H), 4.99 (t, J=9.4 Hz, 1H), 5.52 (m, 1H), 5.80 (q, J=8.8 Hz, 1H), 7.08 (s, 1H), 7.17 (m, 2H), 7.54 (s, 1H), 7.84 (d, J=9.2 Hz, 1H), 10.3 (s, 1H).

Sources & evidence

ORD record
ord-d8ea88ac43ce4492bfed6a4651b2cb54
Source dataset
uspto-grants-2011_08
Patent number
US07989471B2

Reaction notes

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