1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86648457, compound

HRID 43438Notes

Reaction equation

HRID 43438 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:12]=2)[CH2:4][C@H:3]1[O:18][CH3:19].[Cl:20][C:21]1[N:22]=[C:23]([C:27](O)=[O:28])[NH:24][C:25]=1[CH3:26].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C>[Cl:20][C:21]1[N:22]=[C:23]([C:27]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[S:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:12]=3)[CH2:4][C@H:3]2[O:18][CH3:19])=[O:28])[NH:24][C:25]=1[CH3:26]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 144742774-chloro-5-methyl-1H-imidazole-2-carboxylic acidHCID 86648458Ethyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 86648457HCID 86648457, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The same operation as in Example (1g) was performed using ethyl cis(±)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate obtained in Example (5d) (0.21 g, 0.73 mmol), 4-chloro-5-methyl-1H-imidazole-2-carboxylic acid obtained in Example (5c) (0.10 g, 0.64 mmol), WSC hydrochloride (0.27 g, 1.41 mmol) and DMAP (10 mg, 0.083 mmol), to obtain 54 mg of the title compound as a pale yellow solid (20%).

Sources & evidence

ORD record
ord-68f0c74a9768429b8c7d7b193fb641ad
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…