Dimethylamine, hydrochloride → HCID 86648872, compound

HRID 1425459Notes

Reaction equation

HRID 1425459 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:23](O)=[O:24])=[CH:21][N:22]=3)[CH2:14][C@H:13]2[O:26][CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.[CH3:29][NH:30][CH3:31].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O.ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:23]([N:30]([CH3:31])[CH3:29])=[O:24])=[CH:21][N:22]=3)[CH2:14][C@H:13]2[O:26][CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86648871cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 86648872HCID 86648872, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

The same operation as in Example (1g) was performed using cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylic acid obtained in Example (11b) (40 mg, 0.09 mmol), dimethylamine hydrochloride (9 mg, 0.11 mmol), WSC hydrochloride (61 mg, 0.32 mmol), HOBT (22 mg, 0.16 mmol), diisopropylethylamine (0.020 mL, 0.12 mmol), dichloromethane (0.75 mL) and DMA (0.75 mL), to obtain 37 mg of the title compound as a white solid (87%).

Sources & evidence

ORD record
ord-4069cf167e4946678b4e6f00004e7625
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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