Sodium Bicarbonate → 2-(dimethylamino)-N-(4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl)acetamide

HRID 8259

Reaktionsgleichung

Reaktionsgleichung von HRID 8259
[CH3:1][N:2]([CH2:4][C:5](Cl)=[O:6])[CH3:3].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:15]([C:22]2[C:31]3[C:26](=[CH:27][C:28]([NH2:32])=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)=[C:16]2[CH2:21][CH2:20][CH2:19][N:17]2[N:18]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([NH:32][C:28]1[CH:27]=[C:26]2[C:31]([C:22]([C:15]3[C:14]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=4)=[N:18][N:17]4[CH2:19][CH2:20][CH2:21][C:16]=34)=[CH:23][CH:24]=[N:25]2)=[CH:30][CH:29]=1)=[O:6]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 70103442-(Dimethylamino)acetyl chlorideHCID 101314164-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-amine

Produkt 1

HCID 101799132-(dimethylamino)-N-(4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of dimethylamino-acetyl chloride (620.0 mg, 13.33 mmol), 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylamine (75 mg, 0.23 mmol), and 4-N,N-dimethylaminopyridine (10.2 mg, 0.09 mmol) in dry pyridine (1 mL) is refluxed for 72 h. The mixture is treated with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer is washed with brine, dried (sodium sulfate), concentrated in vacuo, and the residue chromatographed on SiO2 ((5% to 20% methanol in dichloromethane) to yield a yellow oil, 62.3 mg (67%).

Aufarbeitung

  1. temperatureis refluxed for 72 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customthe residue chromatographed on SiO2 ((5% to 20% methanol in dichloromethane)
  7. customto yield a yellow oil, 62.3 mg (67%)

Quellen und Nachweise

ORD-Eintrag
ord-e9568a52249c4b2fbdc93d52e5bffe68
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

Verknüpfte Notizen

Wird geladen…