Trifluoroacetic acid → Ethyl 8-(1-acetyl-piperidin-4-yl)amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 44596

Reaktionsgleichung

Reaktionsgleichung von HRID 44596
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[C:21]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)(=[O:23])[CH3:22].C(O)(C(F)(F)F)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>CN(C)C=O>[C:21]([N:24]1[CH2:29][CH2:28][CH:27]([NH:1][C:2]2[N:11]=[CH:10][C:9]3[CH2:8][CH2:7][C:6]4[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=4[C:4]=3[N:3]=2)[CH2:26][CH2:25]1)(=[O:23])[CH3:22]

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 122563N-Acetyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 24993827ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Produkt 1

HCID 45141159Ethyl 8-(1-acetyl-piperidin-4-yl)amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 5.187 g (19 mmol) of ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in dry dimethylformamide (120 mL), were added 1-acetyl-4-piperidone (4.7 mL, 38 mmol), CF3COOH (10 mL, 128 mmol) and NaBH(OAc)3 (8.862 g, 42 mmol). After 18 hours, NaOH 0.33N (800 mL, 264 mmol) was added dropwise to the mixture. The precipitate was filtered, washed with water and dried in oven to dryness to give 5.3 g (70% yield) of the title compound.

Aufarbeitung

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried in oven to dryness

Quellen und Nachweise

ORD-Eintrag
ord-061067fb3a22442db40a376ffbe1000a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541429B2

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