Diisopropylethylamine → 2-Bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204310ノート

反応式

HRID 2204310 の反応式
[Br:1][C:2]1[N:6]([CH2:7][CH3:8])[C:5]([CH:9]([NH:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[CH3:25])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:4]([C:26](O)=[O:27])[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>O>[Br:1][C:2]1[N:6]([CH2:7][CH3:8])[C:5]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[N:17]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[CH3:25])[C:26](=[O:27])[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867031155-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid

生成物 1

HCID 867031142-Bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 5-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid (Step K1) (3.11 mmol), TBTU (4.36 mmol) and DIEA (9.33 mmol) was stirred at 80° C. for 1 h. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed successively with H2O and brine, dried (MgSO4), filtered and concentrated. The product was purified by chromatography column to afford the title compound as a colorless oil. tR: 5.90 min (HPLC 4); ESI-MS: tR=1.35 min, [M+H]+ not ionized (LC-MS 1).

後処理

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed successively with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by chromatography column

出典と根拠

ORDレコード
ord-b6c5cb40b4904a68bfb17da43280dfd8
出典データセット
uspto-grants-2016_06
特許番号
US09365576B2

反応ノート

読み込み中…