Piperazin-2-one → HCID 67142728, compound

HRID 574253Notes

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].[NH:36]1[CH2:41][CH2:40][NH:39][CH2:38][C:37]1=[O:42]>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:39]2[CH2:40][CH2:41][NH:36][C:37](=[O:42])[CH2:38]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

Conditions

Temperature: 140 °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 (100 mg, 0.182 mmol) and piperazine-2-one (187 mg, 1.82 mmol) were placed into a microwave flask along the wall of which 1 mL of acetonitrile was then added. The solution was stirred at 140° C. for 3 hrs while being irradiated with microwaves. After concentration in a vacuum, the concentrate was purified by column chromatography eluting with a dichloromethane/methanol (35/1) eluent to afford 60 mg of the compound as a yellowish solid (yield 58%). 1H NMR (300 MHz, CDCl3) δ 1.36 (9H, s), 2.43 (3H, s), 2.86 (1H, m), 3.27 (2H, m), 3.50 (1H, m), 3.74 (1H, m), 4.07 (2H, m), 4.27 (1H, m), 5.04 (1H, m), 5.29 (2H, dd), 5.68 (1H, m), 6.30 (1H, m), 6.90 (2H, t), 7.22-7.37 (6H, m)

Workup

additionwas then added
customwhile being irradiated with microwaves
concentrationAfter concentration in a vacuum
customthe concentrate was purified by column chromatography
washeluting with a dichloromethane/methanol (35/1) eluent

Sources & evidence

ORD record: ord-51f97bd9e07c46ac835c8e79707aeaeb
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034850B2

Reaction notes

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