1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178422노트

반응식

HRID 1178422 반응식
CC[N:3]=C=NCCCN(C)C.[Cl:12][C:13]1[S:39][C:16]2[NH:17][C:18]([C:20]([NH:22][CH:23]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:33][CH:34](O)CO)[C:24]3=[O:38])=[O:21])=[CH:19][C:15]=2[CH:14]=1.ClC1SC2NC(C(NC3CC4C(=CC=CC=4)N(C[C@@H](O)CO)C3=O)=O)=CC=2C=1>C(Cl)Cl>[Cl:12][C:13]1[S:39][C:16]2[NH:17][C:18]([C:20]([NH:22][CH:23]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:33][C:34]#[N:3])[C:24]3=[O:38])=[O:21])=[CH:19][C:15]=2[CH:14]=1

참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 104771912-chloro-N-[1-[(2R)-2,3-dihydroxypropyl]-2-oxo-3,4-dihydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide

생성물 1

HCID 104526402-Chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

EDCI (1.09 g, 5.65 mmol) was added to a suspension of 5-Carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (Method 9, 1.04 g, 5.13 mmol) and (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetonitrile (Method 13; 1.29 g, 5.13 mmol) in DCM (30 mL) and the reaction stirred for 18 hours. The reaction was evaporated and the residue was partitioned between DCM:MeOH (9:1) (100 mL) and aqueous K2CO3 (25 mL). The organic layer was then separated, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:MeOH (9:1)) to give a brown solid. The solid was triturated with refluxing Et2O (25 mL) and the solid filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford the title compound (414 mg, 21%) as a pale brown solid.

후처리

  1. customThe reaction was evaporated
  2. customthe residue was partitioned between DCM:MeOH (9:1) (100 mL) and aqueous K2CO3 (25 mL)
  3. customThe organic layer was then separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (DCM to DCM:MeOH (9:1))
  8. customto give a brown solid
  9. customThe solid was triturated with refluxing Et2O (25 mL)
  10. filtrationthe solid filtered
  11. washwashed with Et2O (25 mL)

출처 및 근거

ORD 기록
ord-a4b7dfa4c70c4964a0a21719ea56d29a
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276517B2

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