1-Benzylpiperazine → HCID 67142847, compound

HRID 574245Notes

Reaction equation

HRID 574245 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14](Br)=[C:13]([CH3:18])[N:12]([CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])[C:11]1=[O:28])([CH3:4])([CH3:3])[CH3:2].[CH2:36]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(#N)C>[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:46]2[CH2:47][CH2:48][N:43]([CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:44][CH2:45]2)=[C:13]([CH3:18])[N:12]([CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])[C:11]1=[O:28])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 11432814tert-butyl N-[(1R)-2-[5-bromo-3-[(2,6-difluorophenyl)methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-phenylethyl]carbamate

Product 1

HCID 67142847HCID 67142847, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

{(R)-2-[5-bromo-3-(2,6-difluoro-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (45 mg, 0.082 mmol), 1-benzyl-piperazine (216 mg, 1.23 mmol), and acetonitrile (500 μl) were placed in a microwave vessel and heated at 120° C. for 1 hr by microwave irradiation with stirring. Following concentration, the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate, 2/1) and dried in a vacuum to afford the 33 mg of the compound as a colorless oil (yield 62%).

Workup

  1. concentrationconcentration
  2. customthe residue was purified
  3. customdried in a vacuum

Sources & evidence

ORD record
ord-aa8794e2ffcd4ee99a86832df541c80a
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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