Ethyl Bromide → Ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

HRID 29106

反応式

HRID 29106 の反応式
Cl.[C:2]1([C:8]#[C:9][C:10]2[S:14][C:13]([C:15]3[N:16]=[C:17]4[CH:22]=[N:21][CH:20]=[CH:19][N:18]4[C:23]=3[NH2:24])=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:27](Br)[CH3:28].CC(=O)OCC.C(Cl)Cl>CN(C=O)C>[CH2:27]([NH:24][C:23]1[N:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:17]2=[N:16][C:15]=1[C:13]1[S:14][C:10]([C:9]#[C:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:12]=1)[CH3:28]

参加物

6

反応物 4

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 21226138Dichloromethane ethylacetateHCID 693193602-(5-Phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine hydrochloride

生成物 1

HCID 11573751Ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine収率 92.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

395 mg (1.25 mmol) of 2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine hydrochloride (Example 83) were dissolved in DMF (8 ml). After addition of 100 mg (2.5 mmol) of sodium hydride (60% dispersion in mineral oil), the mixture was stirred at RT for 1 h. A solution of 74 μl (0.8 mmol) of ethyl bromide in DMF (2 ml) was then added dropwise. The reaction solution was stirred at RT for 16 h, quenched with water (10 ml) and extracted with EA (2×50 ml). The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 253 mg (0.74 mmol, 58% of theoretical) of ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained by means of column chromatography (silica gel, EA/DCM 4:1).

後処理

  1. stirringThe reaction solution was stirred at RT for 16 h
  2. customquenched with water (10 ml)
  3. extractionextracted with EA (2×50 ml)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under a vacuum

出典と根拠

ORDレコード
ord-bce83af9c2454030b10934d6475f3838
出典データセット
uspto-grants-2008_09
特許番号
US07420056B2

関連ノート

読み込み中…