Ammonium Hydroxide → 4-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxamide

HRID 510073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510073
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:3]=1.O[N:29]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[NH4+]>CN(C=O)C.C(#N)C.O>[NH2:1][C:2]1[C:7]([C:8]([NH2:29])=[O:10])=[CH:6][N:5]=[C:4]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:3]=1

Komponenten

7

Edukt 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66614346HCID 66614346, Verbindung

Produkt 1

HCID 98853504-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

300 mg (0.82 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylic acid (example 102A) and 139 mg (0.91 mmol) of 1-hydroxyl-1H-benzotriazole were dissolved in 2.2 ml of DMF, and 174 mg (0.91 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. While cooling with ice, 140 ml (0.99 mmol) of ammonium hydroxide (28%) were added, and the mixture was reacted at room temperature overnight. 4 ml of acetonitrile/water (1/1) were added and the precipitate formed was filtered off. After drying under high vacuum, 145 mg (48% of theory) of the target compound were obtained.

Aufarbeitung

  1. additionwere added
  2. customthe mixture was reacted at room temperature overnight
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. customAfter drying under high vacuum, 145 mg (48% of theory) of the target compound
  6. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-ce41818563704610b85b1938467ca82f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096592B2

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