3-Aminopropionitrile → 1-(2-Cyano-ethyl)-3-[5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-urea

HRID 2247369Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][C:4]#[N:5].FC1C=C(C2SC(N)=NC=2C)C=CC=1S(C)(=O)=O.[N:24]1([C:29]2[CH:30]=[C:31]([C:39]3[S:43][C:42]([NH:44][C:45](N4C=CN=C4)=[O:46])=[N:41][C:40]=3[CH3:52])[CH:32]=[CH:33][C:34]=2[S:35]([CH3:38])(=[O:37])=[O:36])[CH:28]=[CH:27][N:26]=[CH:25]1>>[C:4]([CH2:3][CH2:2][NH:1][C:45]([NH:44][C:42]1[S:43][C:39]([C:31]2[CH:32]=[CH:33][C:34]([S:35]([CH3:38])(=[O:37])=[O:36])=[C:29]([N:24]3[CH:28]=[CH:27][N:26]=[CH:25]3)[CH:30]=2)=[C:40]([CH3:52])[N:41]=1)=[O:46])#[N:5]

Participants

Reactant 3

HCID 16473-Aminopropionitrile

HCID 573512775-(3-Fluoro-4-(methylsulfonyl)phenyl)-4-methylthiazol-2-amine

HCID 86598422Imidazole-1-carboxylic acid [5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide

Product 1

HCID 865984231-(2-Cyano-ethyl)-3-[5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-urea

Procedure

The titled compound is prepared by the same procedure as example 88, replacing 2-aminoethanol (part 88b) in this example with 3-aminopropionitrile and replacing 5-(3-fluoro-4-methanesulfonyl-phenyl)-2-isocyanato-4-methyl-thiazole (88a) with Imidazole-1-carboxylic acid [5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide (150a)

Sources & evidence

ORD record: ord-426cbbdc70644aa89b90472886ea3c5b
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687637B2

Reaction notes

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