Diisopropylethylamine → HCID 67427797, Verbindung

HRID 23990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23990
[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][C:12]([OH:14])=O.[CH2:15]([O:17][C:18](=[O:34])[CH2:19][CH:20]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([NH2:33])=[CH:30][CH:31]=2)[CH:26]=[CH:25]1)[CH2:21][CH2:22][CH3:23])[CH3:16].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:15]([O:17][C:18](=[O:34])[CH2:19][CH:20]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([NH:33][C:12](=[O:14])[CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[CH2:6][CH2:7][CH2:8][NH:9][C:10]=4[N:1]=3)=[CH:30][CH:31]=2)[CH:26]=[CH:25]1)[CH2:21][CH2:22][CH3:23])[CH3:16]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22570252(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)acetic acidHCID 674273453-(5-Amino-indol-1-yl)-hexanoic acid ethyl ester

Produkt 1

HCID 67427797HCID 67427797, VerbindungAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (5,6,7,8tetrahydro-[1,8]-naphthyridin-2-yl)-acetic acid (0.2 g, 0.65 mmol), 3-(5-amino-indol-1-yl)-hexanoic acid ethyl ester (0.19 g, 0.71 mmol), BOP (0.35 g, 0.78 mmol), and diisopropylethylamine (0.45 mL, 2.6 mmol) in DMF (2.5 mL) was stirred for 16 h. Solvents were evaporated. The resulting residue was partitioned between H2O and EtOAc. The aqueous layer was separated and extracted once more with EtOAc. The extracts were combined, washed with H2O, brine, dried over Na2SO4, concentrated, and flash chromatographed on silica gel, eluting with EtOAc/DCM (15, 30, 50, and 80%) to give the title compound (0.20 g, 67% yield) as a brown oil. Mass spectrum (LCMS, ESI) calculated for C26H33N4O3 449.3 (M+H); found 449.3.

Aufarbeitung

  1. customSolvents were evaporated
  2. customThe resulting residue was partitioned between H2O and EtOAc
  3. customThe aqueous layer was separated
  4. extractionextracted once more with EtOAc
  5. washwashed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customflash chromatographed on silica gel
  9. washeluting with EtOAc/DCM (15, 30, 50, and 80%)

Quellen und Nachweise

ORD-Eintrag
ord-ff41286fcaf54e4da97e50e36fe6d052
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855722B2

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