1-Butanol → 1-(4-(4-(4-(4-(Aminomethyl)piperidin-1-yl)-5-fluoropyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone
Reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30](=[O:32])[CH3:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(O)CCC.[CH3:38][C:39]#[N:40]>>[NH2:40][CH2:39][CH:38]1[CH2:14][CH2:13][N:12]([C:6]2[C:5]([F:9])=[CH:4][N:3]=[C:2]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:25][CH2:26][N:27]([C:30](=[O:32])[CH3:31])[CH2:28][CH2:29]4)=[CH:22][CH:23]=3)[N:7]=2)[CH2:15][CH2:16]1Participants
6
Procedure
A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), 4-N-Boc-aminomethyl piperidine (214 mg, 1.00 mmol) and triethylamine (0.300 mL, 2.15 mmol) in CH3CN (4 mL) was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (6 mL). 2 mL of the nBuOH solution was taken, to which 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (108 mg, 0.49 mmol) was added. The solution was stirred at 116° C. for 20 h. nBuOH was removed in vacuo. The residue was dissolved in TFA (2 mL). After being stirred at room temperature for 2 h, TFA was removed in vacuo. The residue was purified by HPLC to give the titled compound (43 mg). MS 428.6 (M+H); UV 206.8, 265.8 nm.
Workup
- concentrationIt was concentrated in vacuo
- dissolutionThe residue was dissolved in nBuOH (6 mL)
- additionwas added
- customwas removed in vacuo
- dissolutionThe residue was dissolved in TFA (2 mL)
- stirringAfter being stirred at room temperature for 2 h
- customTFA was removed in vacuo
- customThe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-657bdb18136f47e28fdc88b5e1b3b521
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139581B2
Reaction notes
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