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

反応式

HRID 43949 の反応式
[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]

参加物

7

反応物 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

生成物 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-carboxylate収率 81.3%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 85741463dichloromethane N,N-dimethylacetamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9709f6803c124b358681070d3a0289e4
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

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