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-[17-[2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-(cyclopropyl)sulfonamide

HRID 1669582Notes

Reaction equation

HRID 1669582 reaction equation
C(C1N=C(C2C=C(OC3CC4N(C(=O)CCCCCC=CC5C(C(O)=O)(NC4=O)C5)C3)C3C(=C(C)C(OC)=CC=3)N=2)SC=1)(C)C.[CH:46]([C:49]1[N:50]=[C:51]([C:54]2[CH:63]=[C:62]([O:64][CH:65]3[CH2:83][CH:82]4[N:67]([C:68](=[O:94])[CH2:69]C[CH2:71][CH2:72][CH2:73][CH2:74][CH:75]=[CH:76][CH:77]5[C:79]([C:85]([NH:87][S:88]([CH:91]6[CH2:93][CH2:92]6)(=[O:90])=[O:89])=[O:86])([NH:80][C:81]4=[O:84])[CH2:78]5)[CH2:66]3)[C:61]3[C:56](=[CH:57][C:58]([O:95][CH3:96])=[CH:59][CH:60]=3)[N:55]=2)[S:52][CH:53]=1)([CH3:48])[CH3:47]>>[CH:46]([C:49]1[N:50]=[C:51]([C:54]2[CH:63]=[C:62]([O:64][CH:65]3[CH2:83][CH:82]4[N:67]([C:68](=[O:94])[CH2:69][CH2:71][CH2:72][CH2:73][CH2:74][CH:75]=[CH:76][CH:77]5[C:79]([C:85]([NH:87][S:88]([CH:91]6[CH2:92][CH2:93]6)(=[O:90])=[O:89])=[O:86])([NH:80][C:81]4=[O:84])[CH2:78]5)[CH2:66]3)[C:61]3[C:56](=[CH:57][C:58]([O:95][CH3:96])=[CH:59][CH:60]=3)[N:55]=2)[S:52][CH:53]=1)([CH3:48])[CH3:47]

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 67318953HCID 67318953, compound

Product 1

HCID 67317849N-[17-[2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-(cyclopropyl)sulfonamide

Procedure

The title compound was prepared from 17-[2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid (62) 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=722 (M+H)+. 1H NMR (CDCl3): 0.99-1.77 (m, 17H), 1.94 (dd, J=6.0 Hz, J=9.7 Hz, 1H), 2.12-2.26 (m, 2H), 2.37 (dd, J=7.3 Hz, 16.4 Hz, 1H), 2.57-2.71 (m, 3H), 2.96 (m, 1H), 3.04 (m, 1H), 3.22 (m, 1H), 3.92 (m, 1H), 3.96 (s, 3H), 4.14 (dd, J=3.7 Hz, 11.3 Hz, 1H), 4.58 (t, J=7.9 Hz, 1H), 5.05 (t, J=10.6 Hz, 1H), 5.53 (m, 1H), 5.66 (m, 1H), 6.58 (s, 1H), 7.06 (s, 1H), 7.12 (dd, J=2.5 Hz, J=9.1 Hz, 1H), 7.37 (d, J=2.5 Hz, 1H), 7.56 (s, 1H), 7.93 (d, J=9.1 Hz, 1H), 10.8 (br s, 1H).

Sources & evidence

ORD record
ord-8856ca1b527a48348c753fc5962fb3cf
Source dataset
uspto-grants-2011_08
Patent number
US07989471B2

Reaction notes

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