Diisopropylethylamine → HCID 22222398, compound

HRID 1794964Notes

Reaction equation

HRID 1794964 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=O)[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].Cl.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([N:27]1[CH2:32][CH2:31][NH:30][CH:29]([CH3:33])[C:28]1=[O:34])(=[O:26])=[O:25])([O-:17])=[O:16].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>[CH3:33][CH:29]1[N:30]([C:11](=[O:13])[CH2:10][N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH2:31][CH2:32][N:27]([S:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N+:15]([O-:17])=[O:16])(=[O:25])=[O:26])[C:28]1=[O:34]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 2724699PyBOPHCID 68799216HCID 68799216, compound

Product 1

HCID 22222398HCID 22222398, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (thymin-1-yl)-acetic acid (55 mg, 0.30 mmol), 1-(2-nitro-benzenesulfonyl)-3-methyl-piperazin-2-one HCl salt (100 mg, 0.30 mmol), and PyBOP (156 mg, 0.45 mmol) in DMF (1 mL) was added N,N-diisopropylethylamine (0.08 mL) at room temperature. After stirring for additional 2 h at 40° C., the reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in reduced pressure and the residue was purified by column chromatography to give the titled compound (100 mg, 72%). 1H NMR (500 MHz; DMSO-d6) δ 11.31 (s, 1H), 8.33 (d, 1H), 8.10 (d, 1H), 8.04˜7.93 (m, 2H), 7.35 (s, 1H), 4.85˜4.60 (m, 2.5H), 4.55˜4.40 (m, 0.5H), 4.20˜4.10 (m, 0.5H), 4.05˜3.90 (m, 1.5H), 3.78˜3.60 (m, 1H), 3.30 (m, 1H), 1.74 (s, 3H), 1.42 (d, 1H), 1.27 (d, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6c6295eaa1d94626be25c8e8342afd72
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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