Dimethylamine → N,N-Dimethyl-3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionamide

HRID 8270

Reaktionsgleichung

Reaktionsgleichung von HRID 8270
CO[C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:19][N:18]4[CH2:28][CH2:29][CH2:30][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[CH3:32][NH:33][CH3:34].CO.C[Al](C)C.CCCCCC.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>ClCCl>[CH3:32][N:33]([CH3:34])[C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:19][N:18]4[CH2:28][CH2:29][CH2:30][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1

Komponenten

8

Edukt 6

HCID 674DimethylamineHCID 887MethanolHCID 8058HexaneHCID 9855836Potassium sodium tartarateHCID 101799083-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl esterHCID 16682925Trimethylaluminum

Produkt 1

HCID 10274004N,N-Dimethyl-3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl ester (0.30 g, 0.73 mmol) and 2M dimethylamine in methanol (1.05 mL, 2.1 mmol) in dichloromethane (1 mL) is added 2 M trimethylaluminum in hexane (1.64 mL, 3.25 mmol). The solution is heated at 40° C. for 48 h. The mixture is diluted with dichloromethane (150 mL), treated with saturated potassium sodium tartrate (30 mL), and stirred 18 h. The organic portion is separated and; washed with water and brine, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (10% methanol in dichloromethane) to yield the title compound, 0.29 g (89%), as a yellow foam.

Aufarbeitung

  1. customThe organic portion is separated
  2. washwashed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-48783e86a64147d588437490851d74d4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

Verknüpfte Notizen

Wird geladen…