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

HRID 1178421노트

반응식

HRID 1178421 반응식
CCN=C=NCCCN(C)C.ClC1SC2NC(C(NC3CC4C(=CC=CC=4)N(CC(O)CO)C3=O)=O)=CC=2C=1.[Cl:40][C:41]1[S:70][C:44]2[NH:45][C:46]([C:48]([NH:50][CH:51]3[CH2:60][C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[N:53]([CH2:61][C@@H:62]4CO[C:64](C)(C)[O:63]4)[C:52]3=[O:69])=[O:49])=[CH:47][C:43]=2[CH:42]=1>C(Cl)Cl>[Cl:40][C:41]1[S:70][C:44]2[NH:45][C:46]([C:48]([NH:50][CH:51]3[CH2:60][C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[N:53]([CH2:61][CH2:62][O:63][CH3:64])[C:52]3=[O:69])=[O:49])=[CH:47][C:43]=2[CH:42]=1

참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 103895012-Chloro-N-[1-(2,2-dimethyl-1,3-dioxolan-4(R)-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3(R,S)-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 102506062-Chloro-N-{1-[2-(methoxy)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

EDCI (225 mg, 1.17 mmol) was added to a suspension of 5-carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (Method 9, 234 mg, 1.06 mmol) and 3-amino-1-(2-methoxyethyl)-3,4-dihydroquinolin-2(1H)-one (Method 12; 215 mg, 1.06 mmol) in DCM (20 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 water (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 afford the title compound (180 mg, 42%) as a yellow solid.

후처리

  1. customThe reaction was evaporated
  2. customthe residue was partitioned between DCM:MeOH (9:1) (100 mL) and water (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))

출처 및 근거

ORD 기록
ord-dab8c8dd426a43688454168e38c2c3e4
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276517B2

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