Triethylamine → 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetamide

HRID 20637

Reaktionsgleichung

Reaktionsgleichung von HRID 20637
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1.[NH2:21][CH2:22][C:23]([NH2:25])=[O:24].Cl.C(N(CC)CC)C>C(O)C>[CH:15]1([O:14][C:7]2[C:8]([O:12][CH3:13])=[CH:9][CH:10]=[C:11]3[C:6]=2[O:5][C:4](=[O:20])[CH:3]=[C:2]3[NH:21][CH2:22][C:23]([NH2:25])=[O:24])[CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2723639Glycinamide hydrochlorideHCID 771747944-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Produkt 1

HCID 248494302-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (170 mg, 0.58 mmol, Example 7, Step 1), glycinamide•HCl (77 mg, 0.70 mmol), triethylamine (0.2 mL, 1.4 mmol), and ethanol (2 mL) was heated at 75° C. in a sealed vial for 30 h. The reaction was allowed to cool to rt, concentrated, diluted with dichloromethane (10 mL), and let stand. After 10 min, the free-flowing solid was filtered and dried to give 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetamide: 1H NMR (400 MHz, DMSO-d6): δ 7.89 (t, 1H), 7.70 (d, 1H), 7.57 (s, 1H), 7.22 (s, 1H), 7.07 (d, 1H), 4.83 (s, 1H), 4.81 (m, 1H), 3.86 (s, 3H), 3.80 (d, 2H), 1.90-1.48 (m, 8H); MS (ESI): 333.0.

Aufarbeitung

  1. temperatureto cool to rt
  2. concentrationconcentrated
  3. additiondiluted with dichloromethane (10 mL)
  4. filtrationthe free-flowing solid was filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e3442c3a84604f64967529368c0e4771
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745646B2

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