Trifluoroacetic acid → N-(4-(4-methylpiperazin-1-yl)phenyl)-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidin-2-amine

HRID 526055Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.FC(F)(F)C(O)=O>CC(O)CC.ClCCl>[CH3:21][N:22]1[CH2:23][CH2:24][N:25]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:2]3[N:3]=[C:4]([O:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=4)[C:5]4[S:10][CH:9]=[CH:8][C:6]=4[N:7]=3)=[CH:30][CH:29]=2)[CH2:26][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

The compound (12.9 mmol) obtained in Step 3 was dissolved in 2-butanol (70 mL), and 4-(4-methylpiperazin-1-yl)benzeneamine (12.9 mmol) and trifluoroacetic acid (12.9 mmol) were added thereto. The mixture was stirred at 100° C. for 16 hours to complete the reaction, diluted with dichloromethane, and then washed with sat. NaHCO3 aqueous solution. The organic layer was dried with anhydrous sodium sulfate and then filtered and distilled under a reduced pressure. The residue was separated by column chromatography (dichloromethane:methanol=20:1 (volume ratio)) to obtain the title compound (yield: 42%).

Workup

customthe reaction
washwashed with sat. NaHCO3 aqueous solution
dry with materialThe organic layer was dried with anhydrous sodium sulfate
filtrationfiltered
distillationdistilled under a reduced pressure
customThe residue was separated by column chromatography (dichloromethane:methanol=20:1 (volume ratio))

Sources & evidence

ORD record: ord-5fa8f8f4b259488da38bc7a03c34466b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345719B2

Reaction notes

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