Diisopropylethylamine → 1-(2-Nitro-benzenesulfonyl)-4-[(thymin-1-yl)-acetyl]-piperazin-2-one

HRID 1794948Notes

Reaction equation

HRID 1794948 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C:15]1=[O:20])(=[O:13])=[O:12])([O-:4])=[O:3].[N:21]1([CH2:30][C:31](O)=[O:32])[CH:29]=[C:27]([CH3:28])[C:25](=[O:26])[NH:24][C:22]1=[O:23].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(O)C>[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:31](=[O:32])[CH2:30][N:21]2[CH:29]=[C:27]([CH3:28])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:16][C:15]1=[O:20])(=[O:12])=[O:13])([O-:4])=[O:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 2724699PyBOPHCID 688024401-(2-Nitrobenzenesulfonyl)-piperazin-2-one HCl salt

Product 1

HCID 222223791-(2-Nitro-benzenesulfonyl)-4-[(thymin-1-yl)-acetyl]-piperazin-2-oneYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (1.13 g, 3.5 mmol), (thymin-1-yl)-acetic acid (0.64 g, 3.5 mmol), and PyBOP (2.00 g, 3.85 mmol) in DMF (11 mL) was addeed N,N-diisopropylethylamine (0.91 mL) at room temperature. After stirring for additional 2 h, the reaction mixture was slowly added to a solution of aqueous ethyl alcohol to precipitate solid. The solid was filtered off, washed with ethanol and ethyl ether, and dried in vacuo to give the titled compound (1.50 g, 95%).

Workup

  1. customat room temperature
  2. customto precipitate solid
  3. filtrationThe solid was filtered off
  4. washwashed with ethanol and ethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-56978464fef94c6abe740877e6e7a1e0
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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