4-Methylmorpholine → Ethyl 2-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propylcarbamoyl]-acetate

HRID 617903

Reaktionsgleichung

Reaktionsgleichung von HRID 617903
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][NH2:14].C([CH:17]([C:21]([OH:23])=O)[C:18]([OH:20])=[O:19])C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:35]2C=CC=C[C:34]=2N=N1.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][NH:14][C:21]([CH2:17][C:18]([O:20][CH2:34][CH3:35])=[O:19])=[O:23]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 11756Ethylmalonic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 98775993-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine

Produkt 1

HCID 21850003Ethyl 2-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propylcarbamoyl]-acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-8 (0.068 g, 0.36 mmol), ethylmalonic acid (0.052 g, 0.40 mmol), BOP (0.24 g, 0.54 mmol), and NMM (0.16 mL, 1.4 mmol) in DMF (1.8 mL) was stirred at ambient temperature for 20 h. The mixture was diluted with ethyl acetate, washed with water, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed on silica gel, eluting with 15% ethanol/EtOAc to give 1-9 as a colorless glass.

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed on silica gel
  5. washeluting with 15% ethanol/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-532b10e154474506ac8549ea4b856d4a
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952341

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