N-methyliminodiacetic acid → 1-[4-(2,4-Dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]-4-methylpiperazine-2,6-dione

HRID 1823476

Reaktionsgleichung

Reaktionsgleichung von HRID 1823476
[NH2:1][C:2]1[C:3]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])=[N:4][C:5]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)=[N:6][CH:7]=1.[CH3:29][N:30]([CH2:35][C:36](O)=[O:37])[CH2:31][C:32](O)=[O:33].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:3]1[C:2]([N:1]2[C:36](=[O:37])[CH2:35][N:30]([CH3:29])[CH2:31][C:32]2=[O:33])=[CH:7][N:6]=[C:5]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)[N:4]=1

Komponenten

5

Edukt 4

HCID 20441N-methyliminodiacetic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22142671[5-Amino-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))-amino]ethyl}amine

Produkt 1

HCID 98070351-[4-(2,4-Dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]-4-methylpiperazine-2,6-dione

Versuchsvorschrift

1 mmol of [5-amino-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine, and 2 mmol of methyliminodiacetic acid, 4 mmol of HBTU, and 5 mmol of N,N-diisopropylethylamine were added to solution and stirred for six hours at room temperature. The reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The solution was extracted three times with ethyl acetate, dried over sodium sulfate, purified by column chromatography eluting with 5-10% methanol/methylene chloride to obtain 1-[4-(2,4-dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]-4-methylpiperazine-2,6-dione.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water and ethyl acetate
  3. extractionThe solution was extracted three times with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. custompurified by column chromatography
  6. washeluting with 5-10% methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-aa04c29f296445979560ffe209f36377
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037918B2

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