Reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[F:18][C:19]([F:25])([F:24])[CH2:20][CH2:21][CH2:22][NH2:23].C1(N=C=NC2CCCCC2)CCCCC1>CS(C)=O>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([NH:23][CH2:22][CH2:21][CH2:20][C:19]([F:25])([F:24])[F:18])=[O:17])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]Participants
5
Procedure
1 mmol from theophylline-7-acetic acid (238 mg) and 4,4,4-trifluorobutan-1-amine (127 mg) was dissolved in 3 ml of DMSO. An equimolar amount of N,N′-dicyclohexylcarbodiimide (206 mg) was added and the solution was stirred for 48 h at ambient temperature. The solvent was filtered and concentrated under high vacuum. The oily residue, dissolved in minimal amount of ethyl acetate was subjected to flash chromatography. The following eluents were used: ethyl acetate:petroleum ether (2:1), ethyl acetate and ethyl acetate:methanol (9:1). The fractions containing the new spot (Rf=0.07, TLC, ethyl acetate) were collected and evaporated. The white powder was recrystallized from ethyl acetate/petroleum ether.
Workup
- filtrationThe solvent was filtered
- concentrationconcentrated under high vacuum
- dissolutionThe oily residue, dissolved in minimal amount of ethyl acetate
- additionThe fractions containing the new spot (Rf=0.07, TLC, ethyl acetate)
- customwere collected
- customevaporated
- customThe white powder was recrystallized from ethyl acetate/petroleum ether
Sources & evidence
- ORD record
- ord-d8e0ff2ab4ef43bfb4ba66883ac6dc5e
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296691B2
Linked notes
Loading…