4-Methylmorpholine → HCID 68405881, compound

HRID 43878Notes

Reaction equation

HRID 43878 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[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:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[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 67548698Ethyl 2-(3-aminoazetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 68405881HCID 68405881, compoundYield 64%

Procedure

The same operation as in Example (217c) was performed using ethyl 2-(3-aminoazetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (218b) (144 mg, 0.60 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (104 mg, 0.60 mmol), WSC hydrochloride (343 mg, 1.79 mmol), 1-hydroxybenzotriazole (81 mg, 0.60 mmol) and N-methylmorpholine (0.13 mL, 1.19 mmol), to obtain 151 mg of the title compound as a white solid (64%).

Sources & evidence

ORD record
ord-95bc4671c4314b97be9539e926359048
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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