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

HRID 2247386Notes

Reaction equation

HRID 2247386 reaction equation
C(OC(=O)CCCNC(NC1SC(C2C=CC(S(C)(=O)=O)=C(F)C=2)=C(C)N=1)=O)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[S:41][C:40]([NH2:42])=[N:39][C:38]=2[CH3:43])=[CH:33][C:32]=1[S:44]([CH3:47])(=[O:46])=[O:45].[CH2:48]([O:50][C:51](=[O:57])[CH2:52][CH2:53][N:54]=[C:55]=[O:56])[CH3:49]>>[CH2:48]([O:50][C:51](=[O:57])[CH2:52][CH2:53][NH:54][C:55]([NH:42][C:40]1[S:41][C:37]([C:34]2[CH:35]=[CH:36][C:31]([Cl:30])=[C:32]([S:44]([CH3:47])(=[O:45])=[O:46])[CH:33]=2)=[C:38]([CH3:43])[N:39]=1)=[O:56])[CH3:49]

Participants

4

Reactant 3

HCID 2733373Ethyl 3-isocyanatopropanoateHCID 578311165-[4-Chloro-3-(methylsulfonyl)phenyl]-4-methyl-1,3-thiazol-2-amineHCID 865984314-{3-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido)-butyric acid ethyl ester

Product 1

HCID 865984373-{3-[5-(4-Chloro-3-methanesulfonyl-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-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 83) and replacing ethyl-4-isocyanatobutyrate with 3-isocyanato-propionic acid ethyl ester.

Sources & evidence

ORD record
ord-871d54b1a6f445f5bd8422bbe69b3da5
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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