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 1178440ノート

反応式

HRID 1178440 の反応式
[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

参加物

6

反応物 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

生成物 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-carboxamide収率 69.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-75c68cd72d4f4545834d7cf621c9106c
出典データセット
uspto-grants-2007_10
特許番号
US07276517B2

反応ノート

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