Nicotinic Acid → N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

HRID 79590

Reaktionsgleichung

Reaktionsgleichung von HRID 79590
Cl[C:2]1[CH:7]=C[C:5]([C@@H:8](CNC(C)C)[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][CH:24]=[C:25]([NH:26]C(=O)CCC)[C:18]=34)[CH2:13][CH2:12]2)=O)=[CH:4][CH:3]=1.[C:37]([OH:45])(=O)[C:38]1[CH:43]=[CH:42][CH:41]=[N:40][CH:39]=1.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CO.[Li+].[OH-]>[CH2:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:23][CH:24]=[C:25]([NH:26][C:37](=[O:45])[C:38]4[CH:43]=[CH:42][CH:41]=[N:40][CH:39]=4)[C:18]=23)[CH2:13][CH2:12]1)[C:8]1[CH:7]=[CH:2][CH:3]=[CH:4][CH:5]=1

Komponenten

8

Edukt 4

HCID 938Nicotinic AcidHCID 8471Triethylamine2×HCID 10340Sodium CarbonateHCID 44199250(S)-N-(4-(4-(2-(4-chlorophenyl)-3-(isopropylamino)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridin-3-yl)butyramide

Produkt 1

HCID 68760686N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamideAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3939Lithium HydroxideLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Crude 4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.200 g, 0.651 mmol, see Example 25), nicotinic acid (0.0961 g, 0.781 mmol) and triethylamine (0.453 mL, 3.25 mmol) were placed in DMF (3 mL) at room temperature. Triethylamine (0.453 mL, 3.25 mmol) was then added, and the reaction was stirred for 1 hour at room temperature. The reaction was then diluted with MeOH (5 mL), and 3M LiOH (0.5 mL) was added and stirred for 10 minutes. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:20-500:30 DCM:MeOH) to give N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.160 g, 59.6% yield).

Aufarbeitung

  1. additionwas added
  2. stirringstirred for 10 minutes
  3. extractionextracted into DCM
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude residue that
  8. customwas purified by column chromatography (500:20-500:30 DCM:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-28b8a1ddc7934aa48fe7cedccbd0a135
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841304B2

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