4-Methylmorpholine → HCID 86648824, compound

HRID 1425412Notes

Reaction equation

HRID 1425412 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])=[CH:10][CH:9]=2)[CH2:4][C@H:3]1[O:17][CH3:18].[Cl:19][C:20]1[N:21]=[C:22]([C:27](O)=[O:28])[NH:23][C:24]=1[CH2:25][CH3:26].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:19][C:20]1[N:21]=[C:22]([C:27]([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])=[CH:10][CH:9]=3)[CH2:4][C@H:3]2[O:17][CH3:18])=[O:28])[NH:23][C:24]=1[CH2:25][CH3:26]

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 86648825HCID 86648825, compound

Product 1

HCID 86648824HCID 86648824, compoundYield 50.2%

Procedure

The same operation as in Example (221c) was performed using methyl cis(±)-5-(4-amino-3-methoxypiperidin-1-yl)thiophene-2-carboxylate obtained in Example (244c) (76 mg, 0.28 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (54 mg, 0.31 mmol), WSC hydrochloride (162 mg, 0.84 mmol), 1-hydroxybenzotriazole (38 mg, 0.28 mmol) and N-methylmorpholine (0.06 mL, 0.56 mmol), to obtain 60 mg of the title compound as a pale brown solid (50%).

Sources & evidence

ORD record
ord-9f01c3a7b0894ed7b5897f47e0749711
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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