Water → 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-yloxy)ethanone

HRID 1055175

Reaktionsgleichung

Reaktionsgleichung von HRID 1055175
[H-].[Na+].[N:3]1[CH:4]=[CH:5][N:6]2[CH2:11][CH:10]([OH:12])[CH2:9][CH2:8][C:7]=12.Cl[CH2:14][C:15]([N:17]1[CH2:36][CH2:35][C:20]2[N:21]=[C:22]([NH:25][CH:26]3[CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27]3)[N:23]=[CH:24][C:19]=2[CH2:18]1)=[O:16].O>CN(C)C=O>[CH2:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:34][CH:26]1[NH:25][C:22]1[N:23]=[CH:24][C:19]2[CH2:18][N:17]([C:15](=[O:16])[CH2:14][O:12][CH:10]3[CH2:11][N:6]4[CH:5]=[CH:4][N:3]=[C:7]4[CH2:8][CH2:9]3)[CH2:36][CH2:35][C:20]=2[N:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 252091725H,6H,7H,8H-imidazo[1,2-a]pyridin-6-olHCID 867265282-chloro-1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]ethanone

Produkt 1

HCID 904239611-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-yloxy)ethanoneAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Add sodium hydride (0.054 g; 1.85 equiv; 1.35 mmoles) to a solution of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol (0.252 g; 2.0 equiv; 1.46 mmoles) in dimethylformamide (2 mL) and stir at room temperature for 10 minutes. Add this mixture to a 0° C. solution of 2-chloro-1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]ethanone (0.25 g; 1.0 equiv; 0.729 mmoles) in dimethylformamide (2 mL). Stir the resulting solution at 0° C. for 1 hour, then add water and load onto a SCX ion exchange column. Elute off the crude product (methanol to 7N ammonia in methanol). Further purify the product by reverse phase chromatography to afford 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-yloxy)ethanone (0.035 g; 11%) as a white foam. MS (m/z): 445(M+1).

Aufarbeitung

  1. stirringStir the resulting solution at 0° C. for 1 hour
  2. washElute off the crude product (methanol to 7N ammonia in methanol)
  3. customFurther purify the product by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0578b53b67954bfa9691fb67601f314a
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394317B2

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