2-Naphthoxyacetic acid → 1-[2-(2-Naphthyloxy)acetyl]-4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]homopiperazine

HRID 1768947

Reaktionsgleichung

Reaktionsgleichung von HRID 1768947
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]([OH:15])=O.[N:16]1([C:21]2[N:26]=[C:25]([N:27]3[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:24]=[C:23]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[N:22]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]([N:30]1[CH2:31][CH2:32][CH2:33][N:27]([C:25]2[CH:24]=[C:23]([N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[N:22]=[C:21]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[N:26]=2)[CH2:28][CH2:29]1)=[O:15]

Komponenten

4

Edukt 2

HCID 84222-Naphthoxyacetic acidHCID 189463011-[2,6-Di(1-pyrrolidinyl)-4-pyrimidinyl]homopiperazine

Produkt 1

HCID 189462861-[2-(2-Naphthyloxy)acetyl]-4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]homopiperazineAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(2-naphthyloxy)acetic acid (1.1 g, 5.0 mmol) in anhydrous tetrahydrofuran (25 ml) carbonyl-diimidazole (0.80 g, 5.0 mmol) was added in portions, under stirring at room temperature. After 15 minutes a solution of 1-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]homopiperazine (1.58 g, 5.0 mmol) in anhydrous tetrahydrofuran (15 ml) was added dropwise. The mixture was stirred at room temperature for 8 hours and the solvent was distilled off under reduced pressure. The residue was dissolved in methylene chloride, the solution was washed three times with water, dried over MgSO4 and concentrated. The obtained crude product was chromatographed over a silica gel column eluting with a 1:2 mixture of benzene and ethyl acetate to afford 0.7 g of the title compound, yield: 28%, mp. 103°-110° C.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 8 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washthe solution was washed three times with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe obtained crude product
  8. customwas chromatographed over a silica gel column
  9. washeluting with a 1:2 mixture of benzene and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d6156057814448ad884c7ca6105d4e1e
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380724

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