4-Methylmorpholine → Methyl cis(+/-)-5-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-methylthiophene-2-carboxylate

HRID 43943Notes

Reaction equation

HRID 43943 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[C:10]([CH3:17])[CH:9]=2)[CH2:4][C@H:3]1[O:18][CH3:19].[Cl:20][C:21]1[N:22]=[C:23]([C:28](O)=[O:29])[NH:24][C:25]=1[CH2:26][CH3:27].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:20][C:21]1[N:22]=[C:23]([C:28]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[C:10]([CH3:17])[CH:9]=3)[CH2:4][C@H:3]2[O:18][CH3:19])=[O:29])[NH:24][C:25]=1[CH2:26][CH3:27]

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 86648828HCID 86648828, compound

Product 1

HCID 86648827Methyl cis(+/-)-5-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-methylthiophene-2-carboxylateYield 86%

Procedure

The same operation as in Example (221c) was performed using methyl cis(±)-5-(4-amino-3-methoxypiperidin-1-yl)-3-methylthiophene-2-carboxylate obtained in Example (245c) (50 mg, 0.18 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (46 mg, 0.26 mmol), WSC hydrochloride (101 mg, 0.53 mmol), 1-hydroxybenzotriazole (26 mg, 0.19 mmol) and N-methylmorpholine (0.04 mL, 0.35 mmol), to obtain 67 mg of the title compound as a white solid (86%).

Sources & evidence

ORD record
ord-e6b0db797eb5430d92a6e2bf8be3df60
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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