Diisopropylethylamine → HCID 22222408, compound

HRID 1794965Notes

Reaction equation

HRID 1794965 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]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:28]1=[O:39])(=[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>[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][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])[CH:29]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:28]1=[O:39])(=[O:25])=[O:26])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 2724699PyBOPHCID 68802264HCID 68802264, compound

Product 1

HCID 22222408HCID 22222408, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (thymin-1-yl)-acetic acid (13 mg, 0.071 mmol), 1-(2-nitro-benzenesulfonyl)-3-phenyl-piperazin-2-one HCl salt (28 mg, 0.070 mmol), and PyBOP (40 mg, 0.077 mmol) in DMF (0.3 mL) was added N,N-diisopropylethylamine (0.018 mL) at room temperature. After stirring for additional 27 h, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography to give the titled compound (16 mg, 43%). 1H NMR (500 MHz; DMSO-d6) δ 11.33 (s, 1H), 8.36 (d, 1H), 8.13 (d, 1H), 8.05˜7.94 (m, 3H), 7.39˜7.29 (m, 5H), 5.93 (s, 1H), 4.87 (d, 1H), 4.67 (d, 1H), 4.22˜4.16 (m, 2H), 3.96 (m, 1H), 3.78 (m, 1H), 1.74 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-86ea44cbb728473f80552b209da791d4
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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