Reaction equation
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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- stirringThe reaction solution was stirred at RT for 16 h
- customquenched with water (10 ml)
- extractionextracted with EA (2×50 ml)
- dry with materialThe combined organic phases were dried over MgSO4
- filtrationfiltered
- customevaporated under a vacuum
Sources & evidence
- ORD record
- ord-bce83af9c2454030b10934d6475f3838
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420056B2
Linked notes
Loading…