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2-Pyrrolidone → 1-Benzyl-N-(3,4-difluorobenzyl)-6-(3,4-dihydro-2H-pyrrol-5-ylamino)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide

HRID 40149
ノート
印刷プレビュー

反応式

HRID 40149 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=O.O=P(Cl)(Cl)Cl.[NH2:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([C:32]([NH:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[C:38]([F:43])[CH:37]=3)=[O:33])=[C:18]([CH:29]([CH3:31])[CH3:30])[N:19]2[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:15][C:14]=1[F:44]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:22]([N:19]1[C:20]2[C:16](=[CH:15][C:14]([F:44])=[C:13]([NH:12][C:2]3[CH2:3][CH2:4][CH2:5][N:1]=3)[CH:21]=2)[C:17]([C:32]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([F:43])[CH:37]=2)=[O:33])=[C:18]1[CH:29]([CH3:30])[CH3:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 120252-PyrrolidoneHCID 24813Phosphorus oxychlorideHCID 597624006-amino-1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide2 回

生成物 1

HCID 597624361-Benzyl-N-(3,4-difluorobenzyl)-6-(3,4-dihydro-2H-pyrrol-5-ylamino)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide

試薬・触媒・溶媒 2

HCID 1140Toluene
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-pyrrolidinone (47 mg, 0.55 mmol) and POCl3 (0.10 ml, 1.1 mmol) was stirred at 0° C. to room temperature for 2h. To the above mixture was then added a solution of 6-amino-1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide (Compound 172, 50 mg, 0.11 mmol) in toluene (3 ml). The reaction was heated to 110° C. for 16 h and was cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by reverse phase chromatography on C18 bonded silica gel (MeOH) to yield the title compound as a white solid.

後処理

  1. temperaturewas cooled to room temperature
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by reverse phase chromatography on C18 bonded silica gel (MeOH)

出典と根拠

ORDレコード
ord-87efb787dd884b16baaff4567165b540
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524917B2

反応ノート

読み込み中…

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