Dimethylformamide → N-[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide

HRID 1715293Notes

Reaction equation

C(N(CC)CC)C.[NH2:8][C:9]1[S:10][C:11]([C:15]2[N:16]=[C:17]([CH2:20][C:21]#[N:22])[S:18][CH:19]=2)=[C:12]([CH3:14])[N:13]=1.[CH:23]1[N:27]=[CH:26][N:25]([C:28](N2C=NC=C2)=[O:29])[CH:24]=1.CN(C=O)C>C(Cl)Cl>[C:21]([CH2:20][C:17]1[S:18][CH:19]=[C:15]([C:11]2[S:10][C:9]([NH:8][C:28]([N:25]3[CH:24]=[CH:23][N:27]=[CH:26]3)=[O:29])=[N:13][C:12]=2[CH3:14])[N:16]=1)#[N:22]

Participants

Conditions

Temperature: 45 °C

Procedure

Triethylamine (0.65 ml; 4.69 mmol; 1.49 eq.) is added to a suspension of (2′-amino-4′-methyl-4,5′-bi-1,3-thiazol-2-yl)acetonitrile (1 000 mg; 3.15 mmol; 1 eq.) and CDI (1 372.3 mg; 8.46 mmol; 2.68 eq.) in dry DCM (65 ml). DMF (4 ml) is added and the mixture is heated at 45° C. for one night. The reaction is cooled down to rt. The resulting precipitate is filtered and washed with Et2O, affording N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide, which is used in the next step without further purification (822.8 mg; 79%).

Workup

temperatureThe reaction is cooled down to rt
filtrationThe resulting precipitate is filtered
washwashed with Et2O

Sources & evidence

ORD record: ord-6836d492f8d64d95968ef396ef1dd37d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799814B2

Reaction notes

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