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

HRID 1178440노트

반응식

HRID 1178440 반응식
[Cl:1][C:2]1[S:28][C:5]2[NH:6][C:7]([C:9]([NH:11][CH:12]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([CH2:22][CH:23]([OH:26])[CH2:24][OH:25])[C:13]3=[O:27])=[O:10])=[CH:8][C:4]=2[CH:3]=1.[CH:29]1[CH:30]=CC2N(O)N=NC=2[CH:34]=1.CCN=C=NCCCN(C)C.C(CN1C2C(=CC=CC=2)CC(NC(C2NC3SC(Cl)=CC=3C=2)=O)C1=O)(O)=O>CN(C=O)C>[CH3:34][C:29]1([CH3:30])[O:26][CH:23]([CH2:22][N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:21][CH:12]([NH:11][C:9]([C:7]3[NH:6][C:5]4[S:28][C:2]([Cl:1])=[CH:3][C:4]=4[CH:8]=3)=[O:10])[C:13]2=[O:27])[CH2:24][O:25]1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10319016N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-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 21906856N-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide수율 69.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-Carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (Method 9; 243 mg, 1.20 mmol), HOBT (178 mg, 1.32 mmol), anhydrous DMF (10 mL) and finally EDCI (252 mg, 1.32 mmol) were added to 3-amino-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-3,4-dihydroquinolin-2(1H)-one (Method 2, 330 mg, 1.20 mmol) and the reaction was stirred for 18 h. The reaction was evaporated and the residue was dissolved in EtOAc (100 mL) and washed with 1M aqueous HCl (50 mL) and the organic layer was further washed with sat. aqueous NaHCO3 (30 mL) and brine (30 mL). The organic layer was then separated, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (EtOAc:hexanes 1:2) to afford the title compound (382 mg, 69%) as a white solid.

후처리

  1. customThe reaction was evaporated
  2. dissolutionthe residue was dissolved in EtOAc (100 mL)
  3. washwashed with 1M aqueous HCl (50 mL)
  4. washthe organic layer was further washed with sat. aqueous NaHCO3 (30 mL) and brine (30 mL)
  5. customThe organic layer was then separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography (EtOAc:hexanes 1:2)

출처 및 근거

ORD 기록
ord-75c68cd72d4f4545834d7cf621c9106c
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276517B2

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