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

HRID 1715237Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][C:9]1[N:10]=[C:11]([NH2:27])[S:12][C:13]=1[C:14]1[N:15]=[C:16]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[S:17][CH:18]=1.[CH:28]1[N:32]=[CH:31][N:30]([C:33](N2C=NC=C2)=[O:34])[CH:29]=1.CN(C=O)C>C(Cl)Cl>[CH3:8][C:9]1[N:10]=[C:11]([NH:27][C:33]([N:30]2[CH:29]=[CH:28][N:32]=[CH:31]2)=[O:34])[S:12][C:13]=1[C:14]1[N:15]=[C:16]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[S:17][CH:18]=1

Participants

Conditions

Temperature: 45 °C

Procedure

In a 20 ml vial under Ar, triethylamine (51 μl; 0.37 mmol; 1.10 eq.) is added to a stirred suspension of 4′-methyl-2-(morpholin-4-ylcarbonyl)-4,5′-bi-1,3-thiazol-2′-amine, obtained in step II as describe above (142.4 mg; 0.34 mmol; 1 eq.), and CDI (54.4 mg; 0.34 mmol; 1 eq.) in dry DCM (5 ml). DMF (0.30 ml) is added to help the solubility. The mixture is stirred at 45° C. overnight. No starting material can be detected by HPLC. The reaction mixture is cooled down to RT. The resulting precipitate is isolated by filtration, washed with diethyl ether and dried under vacuum, affording Intermediate 7 (107.1 mg; 79%). It is used in the next step without further purification.

Workup

customobtained in step II
temperatureThe reaction mixture is cooled down to RT
customThe resulting precipitate is isolated by filtration
washwashed with diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-c5d5bd451ca74039b5b3947cbb4020e9
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799814B2

Reaction notes

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