Diisopropylethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-(3-ethylphenyl)-2-oxopyrrolidine-3-carboxamide

HRID 58703

反応式

HRID 58703 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:57]([C:59]1[CH:60]=[C:61]([N:65]2[CH2:69][CH2:68][CH:67]([C:70](O)=[O:71])[C:66]2=[O:73])[CH:62]=[CH:63][CH:64]=1)[CH3:58]>CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:70]([CH:67]1[CH2:68][CH2:69][N:65]([C:61]2[CH:62]=[CH:63][CH:64]=[C:59]([CH2:57][CH3:58])[CH:60]=2)[C:66]1=[O:73])=[O:71]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 246893561-(3-Ethylphenyl)-2-oxopyrrolidine-3-carboxylic acid

生成物 1

HCID 49868909N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-(3-ethylphenyl)-2-oxopyrrolidine-3-carboxamide収率 33.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.099 g; 0.428 mmol), PyBOP (0.335 g; 0.643 mmol), N,N-diisopropylethylamine (0.222 mL; 1.29 mmol) and 1-(3-ethylphenyl)-2-oxopyrrolidine-3-carboxylic acid (0.100 g; 0.428 mmol) was stirred in DMF (3 mL) overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.059 g (33%) of the title compound as a white solid.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-ef562a0c2f7b444bb1b0ede4e7085866
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

読み込み中…