Acetic Acid → 3-((2(RS)-(Phenoxymethyl)morpholin-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridine Hydrogen Oxalate

HRID 977079

Reaktionsgleichung

Reaktionsgleichung von HRID 977079
[CH2:1]=[O:2].[O:3]([CH2:10][CH:11]1[O:16][CH2:15][CH2:14][NH:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=[CH:18]1.[OH-:26].[Na+].[C:28]([OH:31])(=[O:30])C>O>[C:28]([OH:31])(=[O:30])[C:1]([OH:26])=[O:2].[O:3]([CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:28][C:19]2[C:20]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:17][CH:18]=2)[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14798Sodium HydroxideHCID 220117952-(Phenoxymethyl)morpholine

Produkt 1

HCID 199644123-((2(RS)-(Phenoxymethyl)morpholin-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridine Hydrogen Oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

38% Aqueous formaldehyde (0.9 ml) was added dropwise to a stirred solution of 2(RS)-(phenoxymethyl)morpholine (2.10 g, 0.0109 mmol) in glacial acetic acid (8 ml) and water (4 ml). After stirring for 10 minutes this solution was treated with 1H-pyrrolo[2,3-b]pyridine (1.18 g, 0.010 mmol). The reaction mixture was stirred at room temperature for 20 hours. The mixture was poured onto 2M sodium hydroxide solution (180 ml) and extracted with ethyl acetate (3×80 ml). The combined extracts were washed with saturated sodium chloride solution (80 ml), dried (sodium sulphate) then evaporated to give a gum which was purified by column chromatography on silica (300 g) using ethyl acetate/methanol (20:1) to afford the title compound free base (2.30 g, 65%) as a gum. The hydrogen oxalate salt had mp 188°-189° C. (ethanol) MS, CI+, m/z=324 for (M+H)+. 1H NMR (360 MHz, DMSO-d6) δ2.55-2.75 (2H, m), 3.14 and 3.30 (each 2H, each 2H, each d, J=12 Hz), 3.86-4.03 (4H, m), 4.08-4.20 (3H, m), 6.84-7.27 (6H, m), 7.46 (1H, s), 8.07 (1H, dd, J1 =1, J2 =8 Hz), 8.27 (1H, dd, J1 =1, J2 =5 Hz), 11.43 (1H, s). Found: C, 60.61; H, 5.43; N, 9.97. C19H21N3O2.C2H2O4 requires C, 61.01; H, 5.61; N, 10.16%.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 20 hours
  2. extractionextracted with ethyl acetate (3×80 ml)
  3. washThe combined extracts were washed with saturated sodium chloride solution (80 ml)
  4. dry with materialdried (sodium sulphate)
  5. customthen evaporated
  6. customto give a gum which
  7. customwas purified by column chromatography on silica (300 g)

Quellen und Nachweise

ORD-Eintrag
ord-e046b6f802c6464da1edbf3fe1c0ce70
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614518

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