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

HRID 1093006Notes

Reaction equation

HRID 1093006 reaction equation
C(OC(=O)CCCNC(NC1SC(C2C=CC(S(C)(=O)=O)=C(F)C=2)=C(C)N=1)=O)C.[NH2:30][C:31]1[S:32][C:33]([C:37]2[CH:42]=[C:41]([Cl:43])[C:40]([S:44]([N:47]([CH3:49])[CH3:48])(=[O:46])=[O:45])=[C:39]([Cl:50])[CH:38]=2)=[C:34]([CH3:36])[N:35]=1.[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:30][C:31]1[S:32][C:33]([C:37]2[CH:42]=[C:41]([Cl:43])[C:40]([S:44](=[O:46])(=[O:45])[N:47]([CH3:49])[CH3:48])=[C:39]([Cl:50])[CH:38]=2)=[C:34]([CH3:36])[N:35]=1)=[O:59])[CH3:52]

Participants

4

Reactant 3

HCID 2733373Ethyl 3-isocyanatopropanoateHCID 865984314-{3-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido)-butyric acid ethyl esterHCID 865984394-(2-Amino-4-methyl-thiazol-5-yl)-2,6-dichloro-N,N-dimethyl-benzenesulfonamide

Product 1

HCID 865984403-{3-[5-(3,5-Dichloro-4-dimethylsulfamoyl-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 4-(2-amino-4-methyl-thiazol-5-yl)-2,6-dichloro-N,N-dimethyl-benzenesulfonamide (171b) and replacing ethyl-4-isocyanatobutyrate with 3-isocyanato-propionic acid ethyl ester.

Sources & evidence

ORD record
ord-7078f121896d44f6b11f623a054373a5
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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