Isobutyraldehyde → N-Methyl-4-[6-(2-methylpropyl)-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzamide

HRID 1364141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364141
[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:19]=[C:18]3[C:12]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)=[N:11]2)=[CH:6][CH:5]=1.[CH3:21][CH:22]([CH3:25])[CH:23]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:19]=[C:18]3[C:12]([CH2:13][CH2:14][N:15]([CH2:21][CH:22]([CH3:25])[CH3:23])[CH2:16][CH2:17]3)=[N:11]2)=[CH:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66930754N-Methyl-4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide

Produkt 1

HCID 16048694N-Methyl-4-[6-(2-methylpropyl)-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N-methyl-4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide (may be prepared as described in Description 25) (30.0 mg, 0.11 mmol) in dichloromethane (3 ml) was treated with 2-methylpropanal (20.0 μl, 0.22 mmol) and acetic acid (1 drop) and stirred at room temperature. Sodium triacetoxyborohydride (47.0 mg, 0.22 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was diluted with methanol and passed down a SCX cartridge eluting with methanol and then a 2M solution of ammonia in methanol. The basic fractions were combined and evaporated to afford the title compound (E5); MS (ES+) m/e 327 [M+NH3]+.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. washeluting with methanol
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8f58704c55124dd49d4d8b3fcc9832c9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888347B2

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