Thionyl Chloride → Ethyl 2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}phenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 1425042Notes

Reaction equation

HRID 1425042 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:24][C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=2)=[CH:19][CH:18]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[S:24][C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=3)=[CH:21][CH:22]=2)=[O:11])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 58326687Ethyl 2-(4-aminophenyl)-4-methyl-1,3-thiazole-5-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 67548366Ethyl 2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}phenyl)-4-methyl-1,3-thiazole-5-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (50 mg, 0.29 mmol), thionyl chloride (3 mL), pyridine (5 mL) and ethyl 2-(4-aminophenyl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (94b) (113 mg, 0.43 mmol), to obtain 96 mg of the title compound as a pale yellow solid (80%).

Sources & evidence

ORD record
ord-cc396cf99d42418cb88cfcbdaf9f762e
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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