1-Butanol → HCID 44468090, compound

HRID 2381622Notes

Reaction equation

HRID 2381622 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH:10]1[CH2:18][CH2:17][CH2:16][CH:12]([C:13]([NH2:15])=[O:14])[CH2:11]1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(O)CCC>CC#N>[C:32]([N:29]1[CH2:28][CH2:27][N:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:2]3[N:7]=[C:6]([N:10]4[CH2:18][CH2:17][CH2:16][CH:12]([C:13]([NH2:15])=[O:14])[CH2:11]4)[C:5]([F:9])=[CH:4][N:3]=3)=[CH:21][CH:22]=2)[CH2:31][CH2:30]1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 929803-PiperidinecarboxamideHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

Product 1

HCID 44468090HCID 44468090, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), nipecotamide (128 mg, 1.00 mmol) and DEA (0.350 mL, 2.01 mmol) in CH3CN (4 mL) was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (4 mL). 2 mL of the nBuOH solution was taken, to which 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (150 mg, 0.68 mmol) was added. The solution was stirred at 116° C. for 6 h. nBuOH was removed in vacuo. The residue was purified by HPLC to give the titled compound (75 mg). MS 442.4 (M+H); UV 208.8, 261.8 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. dissolutionThe residue was dissolved in nBuOH (4 mL)
  3. additionwas added
  4. customwas removed in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9ba1ee466ec54a7c88d941a64b5f60df
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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