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

HRID 43927Notes

Reaction equation

HRID 43927 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH2:3]1.[Cl:18][C:19]1[N:20]=[C:21]([C:26](O)=[O:27])[NH:22][C:23]=1[CH2:24][CH3:25].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:18][C:19]1[N:20]=[C:21]([C:26]([NH:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]3[S:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=3)[CH2:3]2)=[O:27])[NH:22][C:23]=1[CH2:24][CH3:25]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67548886ethyl 2-[(3S)-3-aminopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 67549733Ethyl 2-[(3S)-3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}pyrrolidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateYield 90%

Procedure

The same operation as in Example (217c) was performed using ethyl 2-[(3S)-3-aminopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (237a) (150 mg, 0.59 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (103 mg, 0.59 mmol), WSC hydrochloride (338 mg, 1.76 mmol), 1-hydroxybenzotriazole (79 mg, 0.59 mmol) and N-methylmorpholine (0.13 mL, 1.17 mmol), to obtain 217 mg of the title compound as a white solid (90%).

Sources & evidence

ORD record
ord-d6889dc019bf4d2b8e6bd7ee33923d1e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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