1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Ethyl cis(+/-)-2-(4-{[(4,5-dichloro-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 1424909Notes

Reaction equation

HRID 1424909 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[Cl: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[Cl:26]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109761024,5-dichloro-1H-imidazole-2-carboxylic AcidHCID 86648458Ethyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate2×

Product 1

HCID 86648461Ethyl cis(+/-)-2-(4-{[(4,5-dichloro-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylateYield 24%

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 by the method described in Example (5d) (0.23 g, 0.81 mmol), 4,5-dichloroimidazole-2-carboxylic acid obtained in Example (7d) (84 mg, 0.46 mmol), WSC hydrochloride (0.24 g, 1.25 mmol) and DMAP (10 mg, 0.083 mmol), to obtain 49 mg of the title compound as a pale yellow solid (24%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-c13bb3a2107d4a80a0cdfcb7194310e6
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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