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

HRID 43960

반응식

HRID 43960 반응식
Cl.[CH3:2][NH2:3].[Cl:4][C:5]1[N:6]=[C:7]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][N:18]([C:21]3[S:22][C:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:24]([CH:26]=O)[N:25]=3)[CH2:17][C@H:16]2[O:33][CH2:34][CH3:35])=[O:13])[NH:8][C:9]=1[CH2:10][CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.ClC(Cl)C.C(OCC)(=O)C>[Cl:4][C:5]1[N:6]=[C:7]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][N:18]([C:21]3[S:22][C:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:24]([CH2:26][NH:3][CH3:2])[N:25]=3)[CH2:17][C@H:16]2[O:33][CH2:34][CH3:35])=[O:13])[NH:8][C:9]=1[CH2:10][CH3:11]

참가 물질

7

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 86648530ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-formyl-1,3-thiazole-5-carboxylate

생성물 1

HCID 86648842Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(methylamino)methyl]-1,3-thiazole-5-carboxylate수율 28.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

3 Å molecular sieves (500 mg) and methylamine hydrochloride (105 mg, 1.55 mmol) were added to a solution of ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-formyl-1,3-thiazole-5-carboxylate obtained in Example (28a) (500 mg, 1.03 mmol) in methanol (5 mL), and the mixture was stirred at room temperature for two hours. The reaction solution was filtered, and then the filtrate was concentrated under reduced pressure. Sodium triacetoxyborohydride (437 mg, 2.06 mmol) was added to a solution of the resulting residue in dichloroethane (10 mL), and the mixture was stirred at room temperature for 20.5 hours. The reaction solution was diluted with ethyl acetate, and then the mixture was extracted with a 1 N aqueous hydrochloric acid solution. A 1 N aqueous sodium hydroxide solution was added to the aqueous layer, followed by extraction with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure to obtain 145 mg of the title compound as a yellow oily substance (28%).

후처리

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. stirringthe mixture was stirred at room temperature for 20.5 hours
  4. extractionthe mixture was extracted with a 1 N aqueous hydrochloric acid solution
  5. additionA 1 N aqueous sodium hydroxide solution was added to the aqueous layer
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  8. filtrationfiltration
  9. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aba2839619da4b08afa5279e96268e42
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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