Ethyl 3-isocyanatopropanoate → 3-{3-[5-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid ethyl ester

HRID 1092999Notes

Reaction equation

HRID 1092999 reaction equation
C(OC(=O)CCCNC(NC1SC(C2C=CC(S(C)(=O)=O)=C(F)C=2)=C(C)N=1)=O)C.[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[S:44][C:43]([NH2:45])=[N:42][C:41]=2[CH3:46])=[CH:36][C:35]=1[C:47]([F:50])([F:49])[F:48])(=[O:33])=[O:32].[CH2:51]([O:53][C:54](=[O:60])[CH2:55][CH2:56][N:57]=[C:58]=[O:59])[CH3:52]>>[CH2:51]([O:53][C:54](=[O:60])[CH2:55][CH2:56][NH:57][C:58]([NH:45][C:43]1[S:44][C:40]([C:37]2[CH:38]=[CH:39][C:34]([S:31]([CH3:30])(=[O:32])=[O:33])=[C:35]([C:47]([F:50])([F:49])[F:48])[CH:36]=2)=[C:41]([CH3:46])[N:42]=1)=[O:59])[CH3:52]

Participants

4

Reactant 3

HCID 2733373Ethyl 3-isocyanatopropanoateHCID 574737494-Methyl-5-(4-(methylsulfonyl)-3-(trifluoromethyl)phenyl)thiazol-2-amineHCID 865984314-{3-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido)-butyric acid ethyl ester

Product 1

HCID 865984333-{3-[5-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid ethyl ester

Procedure

The title compound is prepared by the same procedure as 4-{3-[5-(3-fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-butyric acid ethyl ester (Example 164) by replacing 5-(3-fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 72) with 5-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-ylamine (158a) and replacing ethyl-4-isocyanatobutyrate with 3-isocyanato-propionic acid ethyl ester.

Sources & evidence

ORD record
ord-be071ca77ad1481ab7fc268451db2c90
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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