4-Methylmorpholine → Methyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-ethyl-1,3-thiazole-5-carboxylate

HRID 1425356Notes

Reaction equation

HRID 1425356 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][C:8]([C:13]([O:15][CH3:16])=[O:14])=[C:9]([CH2:11][CH3:12])[N:10]=2)[CH2:3]1.[Cl:17][C:18]1[N:19]=[C:20]([C:25](O)=[O:26])[NH:21][C:22]=1[CH2:23][CH3:24].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:17][C:18]1[N:19]=[C:20]([C:25]([NH:1][CH:2]2[CH2:5][N:4]([C:6]3[S:7][C:8]([C:13]([O:15][CH3:16])=[O:14])=[C:9]([CH2:11][CH3:12])[N:10]=3)[CH2:3]2)=[O:26])[NH:21][C:22]=1[CH2:23][CH3:24]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 68405938Methyl 2-(3-aminoazetidin-1-yl)-4-ethyl-1,3-thiazole-5-carboxylate

Product 1

HCID 67548482Methyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-ethyl-1,3-thiazole-5-carboxylateYield 99%

Procedure

The same operation as in Example (217c) was performed using methyl 2-(3-aminoazetidin-1-yl)-4-ethyl-1,3-thiazole-5-carboxylate obtained in Example (222b) (94 mg, 0.39 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (68 mg, 0.39 mmol), WSC hydrochloride (224 mg, 1.17 mmol), 1-hydroxybenzotriazole (53 mg, 0.39 mmol) and N-methylmorpholine (0.09 mL, 0.78 mmol), to obtain 153 mg of the title compound as a milk white solid (99%).

Sources & evidence

ORD record
ord-a15d9f36a3d74af6ba016267e862cd06
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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