Glycine ethyl ester → 2-(2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetamido) acetamido)acetic acid

HRID 1799149

Reaction equation

HRID 1799149 reaction equation
[Br:1][C:2]1[N:6]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]#[N:18])=[CH:9][CH:8]=2)[C:5]([S:19][C:20]([F:29])([F:28])[C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])=[N:4][CH:3]=1.C([O:32][C:33](=[O:36])[CH2:34][NH2:35])C.BrC1N(C2C3C(=CC=CC=3)C(C#N)=CC=2)C(SC(F)(F)C(O)=O)=NC=1.NCC(NCC(OCC)=O)=O>>[Br:1][C:2]1[N:6]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]#[N:18])=[CH:9][CH:8]=2)[C:5]([S:19][C:20]([F:29])([F:28])[C:21]([NH:23][CH2:24][C:25]([NH:35][CH2:34][C:33]([OH:32])=[O:36])=[O:26])=[O:22])=[N:4][CH:3]=1

Participants

5

Reactant 4

HCID 12176Glycine ethyl esterHCID 124706Ethyl glycylglycinateHCID 592258472-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetamido)acetic acidHCID 592258722-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetic acid

Product 1

HCID 592258702-(2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetamido) acetamido)acetic acid

Procedure

2-(2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetamido)acetamido)acetic acid is prepared via either of the two routes shown below. In the first, 2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetamido)acetic acid (see eg 14) is coupled with glycine ethyl ester and then hydrolyzed to the acid. In the second, (see eg 10), 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetic acid is coupled with NH2-Gly-Gly-OEt, which is then hydrolyzed to the acid.

Sources & evidence

ORD record
ord-af0d98a06f284628a08bf1d12c02bf68
Source dataset
uspto-grants-2013_01
Patent number
US08344012B2

Linked notes

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