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

HRID 1364141Notes

Reaction equation

HRID 1364141 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-8f58704c55124dd49d4d8b3fcc9832c9
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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