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1-Hydroxybenzotriazole → HCID 44194000、化合物

HRID 1804737
ノート
印刷プレビュー

反応式

HRID 1804737 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19](O)=[O:20])=[CH:5]2.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:44]([N:47]1[C:51]2=[N:52][CH:53]=[C:54]([NH2:56])[CH:55]=[C:50]2[CH2:49][CH2:48]1)(=[O:46])[CH3:45]>CN(C=O)C>[C:44]([N:47]1[C:51]2=[N:52][CH:53]=[C:54]([NH:56][C:19]([C:6]3[N:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=4)[C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)=[O:20])[CH:55]=[C:50]2[CH2:49][CH2:48]1)(=[O:46])[CH3:45]
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 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acidHCID 66845730HCID 66845730、化合物

生成物 1

HCID 44194000HCID 44194000、化合物収率 67%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
20 °C

実験手順

To a solution, stirred at 20° C., of 0.28 g (0.97 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid prepared in step 1.1, 186 mg (0.97 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) and 131 mg (0.97 mmol) of 1-hydroxybenzotriazole (HOBT) in 15 mL of DMF are added 206 mg (1.17 mmol) of 1-acetyl-5-amino-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine, prepared in step 1.2. The reaction mixture is stirred for 14 hours at 20° C. and then concentrated under reduced pressure. The resulting product is taken up in 100 mL of water. The suspension is then extracted with three times 30 mL of ethyl acetate. The combined organic phases are washed twice with 20 mL of water, dried over sodium sulfate and then concentrated under reduced pressure. The product obtained is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol. 290 mg of the expected product are thus isolated.

後処理

  1. customprepared in step 1.2
  2. concentrationconcentrated under reduced pressure
  3. extractionThe suspension is then extracted with three times 30 mL of ethyl acetate
  4. washThe combined organic phases are washed twice with 20 mL of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe product obtained
  8. customis purified by chromatography on a column of silica
  9. washeluting with a mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-c6d0f5bf05524669b259a8e1eedc40b4
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354425B2

反応ノート

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