17-[2-Ethoxy-7-methoxyquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid → N-[17-[2-ethoxy-7-methoxyquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)-sulfonamide

HRID 2203469Notes

Reaction equation

HRID 2203469 reaction equation
C(OC1C=C(OC2CC3C(C(=O)N(C)CCCCC=CC4C(C(O)=O)(NC3=O)C4)C2)C2C(=CC(OC)=CC=2)N=1)C.[CH2:41]([O:43][C:44]1[CH:53]=[C:52]([O:54][CH:55]2[CH2:72][CH:71]3[CH:57]([C:58](=[O:84])[N:59]([CH3:83])[CH2:60][CH2:61][CH2:62][CH2:63][CH:64]=[CH:65][CH:66]4[C:68]([C:74]([NH:76][S:77]([CH:80]5[CH2:82][CH2:81]5)(=[O:79])=[O:78])=[O:75])([NH:69][C:70]3=[O:73])[CH2:67]4)[CH2:56]2)[C:51]2[C:46](=[C:47](C)[C:48]([O:85][CH3:86])=[CH:49][CH:50]=2)[N:45]=1)[CH3:42]>>[CH2:41]([O:43][C:44]1[CH:53]=[C:52]([O:54][CH:55]2[CH2:72][CH:71]3[CH:57]([C:58](=[O:84])[N:59]([CH3:83])[CH2:60][CH2:61][CH2:62][CH2:63][CH:64]=[CH:65][CH:66]4[C:68]([C:74]([NH:76][S:77]([CH:80]5[CH2:82][CH2:81]5)(=[O:78])=[O:79])=[O:75])([NH:69][C:70]3=[O:73])[CH2:67]4)[CH2:56]2)[C:51]2[C:46](=[CH:47][C:48]([O:85][CH3:86])=[CH:49][CH:50]=2)[N:45]=1)[CH3:42]

Participants

3

Reactant 2

HCID 6869226917-[2-Ethoxy-7-methoxyquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acidHCID 68696188N-[17-[2-ethoxy-7-methoxy-8-methylquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl] (cyclo-propyl)sulfonamide

Product 1

HCID 68698406N-[17-[2-ethoxy-7-methoxyquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)-sulfonamide

Procedure

The title compound (5) was prepared from 17-[2-ethoxy-7-methoxyquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid (4) following the procedure reported for synthesis of N-[17-[2-ethoxy-7-methoxy-8-methylquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]cyclopropyl)sulfonamide (3): m/z=555 (M+H)+. 1H NMR (CDCl3): 0.80-0.90 (m, 1H), 0.92-1.0 (m, 4H), 1.00-1.3 (m, 3H), 1.41 (t, J=7.1 Hz, 3H), 1.45-1.71 (m, 2H), 1.8-1.95 (m, 4H), 2.21-2.62 (m, 4H), 2.73-2.81 (m, 1H), 2.9-2.94 (m, 1H), 3.0 (s, 3H), 3.31-3.41 (m, 1H), 3.90 (s, 3H), 4.44 (q, J=7.1 Hz, 2H), 5.0-5.08 (m, 2H), 5.6-5.65 (m, 1H), 5.98 (s, 1H), 6.8 (br s, 1H), 7.10 (dd, J=9.1 Hz and J=2.5 Hz, 1H), 7.12 (d, J=2.5 Hz, 1H), 7.28 (s, 1H), 7.9 (d, J=9.1 Hz, 1H), 11.02 (br s, 1H).

Sources & evidence

ORD record
ord-51891b8de1864b5c9ebb8337de87fdc5
Source dataset
uspto-grants-2016_06
Patent number
US09365582B2

Reaction notes

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