Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate → 1-(3-(1-Naphthyloxy)propyl)-3-piperidin-1-yl-1h-indole-2-carboxylic acid

HRID 533250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533250
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[C:16]2[C:30]([O:32]CC)=[O:31])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>[Li+].[OH-].CO.C1COCC1>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[C:16]2[C:30]([OH:32])=[O:31])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 1

HCID 67316989Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate

Produkt 1

HCID 251019521-(3-(1-Naphthyloxy)propyl)-3-piperidin-1-yl-1h-indole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86635511LiOH methanol THFLösungsmittel

Versuchsvorschrift

A mixture of EXAMPLE 74A (30 mg) in 1N aqueous LiOH/methanol/THF (1 mL/1 mL/1 mL) was stirred at room temperature overnight. The reaction mixture was acidified with 1NHCl (1 mL), and extracted with ethyl acetate. The organic phase was dried (Na2SO4) filtered, and concentrated. The concentrate was purified by reverse phaseHPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid). 1H NMR (400 MHz, DMSO-d6) δ 16.82 (s, 1H), 8.08 (d, 1H), 7.96 (d, 1H), 7.85 (d, 1H), 7.69 (d, 1H), 7.48 (m, 3H), 7.36 (t, 1H), 7.24 (m, 1H), 7.13 (t, 1H), 6.83 (t, 1H), 4.89 (t, 2H), 4.16 (t, 2H), 3.24 (br, 4H), 2.33 (m, 2H), 1.70 (br, 6H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by reverse phaseHPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-4584a8b7e4634a3bad0e561930278bd2
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853209B2

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