2-(1-Ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-hydroxycyclopentanecarboxylic acid tert-butyl ester → 17-[2-(2-Cyclohexylthiazol-4-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester

HRID 402185Notes

Reaction equation

HRID 402185 reaction equation
[CH:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:21]=[C:20]([OH:22])[C:19]4[C:14](=[C:15]([CH3:25])[C:16]([O:23][CH3:24])=[CH:17][CH:18]=4)[N:13]=3)[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC(C1CC(O)CC1C(=O)NC1(C(OCC)=O)CC1C=C)=O)(C)(C)C.[CH2:52]([O:54][C:55]([C:57]12[CH2:74][CH:73]1[CH:72]=[CH:71][CH2:70][CH2:69][CH2:68][CH2:67][N:66]([CH3:75])[C:65](=[O:76])[CH:64]1[CH:60]([CH2:61][CH:62](OC3C4C(=C(C)C(OC)=CC=4)N=C(C4C=CC=C(C)N=4)C=3)[CH2:63]1)[C:59](=[O:98])[NH:58]2)=[O:56])[CH3:53]>>[CH2:52]([O:54][C:55]([C:57]12[CH2:74][CH:73]1[CH:72]=[CH:71][CH2:70][CH2:69][CH2:68][CH2:67][N:66]([CH3:75])[C:65](=[O:76])[CH:64]1[CH:60]([CH2:61][CH:62]([O:22][C:20]3[C:19]4[C:14](=[C:15]([CH3:25])[C:16]([O:23][CH3:24])=[CH:17][CH:18]=4)[N:13]=[C:12]([C:10]4[N:11]=[C:7]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)[S:8][CH:9]=4)[CH:21]=3)[CH2:63]1)[C:59](=[O:98])[NH:58]2)=[O:56])[CH3:53]

Participants

4

Reactant 3

HCID 668714182-(1-Ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-hydroxycyclopentanecarboxylic acid tert-butyl esterHCID 6687158517-[2-(6-Methylpyridin-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl esterHCID 178487683HCID 178487683, compound

Product 1

HCID 6687112317-[2-(2-Cyclohexylthiazol-4-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl esterYield 50%

Procedure

The title compound 121 was prepared in 50% yield from 2-(2-cyclohexylthiazol-4-yl)-4-hydroxy-7-methoxy-8-methylquinoline (119) and 2-(1-ethoxycarbonyl-2-vinylcyclo-propylcarbamoyl)-4-hydroxycyclopentanecarboxylic acid tert-butyl ester following the procedure reported for the preparation of 17-[2-(6-methylpyridin-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]-octadec-7-ene-4-carboxylic acid ethyl ester (101): m/z=715 (M+H)+.

Sources & evidence

ORD record
ord-d16c3b0f62024b54a412cbb8570dd39f
Source dataset
uspto-grants-2014_06
Patent number
US08741926B2

Reaction notes

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