Ethylamine → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-(ethylcarbamoyl)-1,3-thiazole-5-carboxylate

HRID 43949

반응식

HRID 43949 반응식
[CH2:1]([NH2:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.[Cl:26][C:27]1[N:28]=[C:29]([C:34]([NH:36][C@H:37]2[CH2:42][CH2:41][N:40]([C:43]3[S:44][C:45]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[C:46]([C:48]([OH:50])=O)[N:47]=3)[CH2:39][C@H:38]2[O:56][CH2:57][CH3:58])=[O:35])[NH:30][C:31]=1[CH2:32][CH3:33]>CC(N(C)C)=O.ClCCl.C(OCC)(=O)C>[Cl:26][C:27]1[N:28]=[C:29]([C:34]([NH:36][C@H:37]2[CH2:42][CH2:41][N:40]([C:43]3[S:44][C:45]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[C:46]([C:48](=[O:50])[NH:3][CH2:1][CH3:2])[N:47]=3)[CH2:39][C@H:38]2[O:56][CH2:57][CH3:58])=[O:35])[NH:30][C:31]=1[CH2:32][CH3:33]

참가 물질

7

반응물 4

HCID 6341EthylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86648529cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid

생성물 1

HCID 86648833Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-(ethylcarbamoyl)-1,3-thiazole-5-carboxylate수율 81.3%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 85741463dichloromethane N,N-dimethylacetamide용매

실험 절차

Ethylamine (2.0 M solution in THF) (0.60 mL, 1.20 mmol), WSC hydrochloride (345 mg, 1.80 mmol) and 1-hydroxybenzotriazole (8 1 mg, 0.60 mmol) were added to a mixed solution of cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid obtained in Example (50a) (300 mg, 0.60 mmol) in DMA/dichloromethane (6 mL/6 mL) at room temperature, followed by stirring for five hours. The reaction solution was diluted with ethyl acetate, and then the mixture was washed with a 1 N aqueous hydrochloric acid solution and 5% saline. The organic layer was dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was suspended and washed in diethyl ether to obtain 257 mg of the title compound as a white solid (81%).

후처리

  1. washthe mixture was washed with a 1 N aqueous hydrochloric acid solution and 5% saline
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washwashed in diethyl ether

출처 및 근거

ORD 기록
ord-9709f6803c124b358681070d3a0289e4
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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