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

HRID 1364140Notes

Reaction equation

HRID 1364140 reaction equation
[CH3:1][N:2]([CH3:21])[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.[CH3:22][CH:23]([CH3:26])[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH3:1][N:2]([CH3:21])[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]([CH2:22][CH:23]([CH3:26])[CH3:24])[CH2:16][CH2:17]3)=[N:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66930795N,N-Dimethyl-4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide

Product 1

HCID 16049737N,N-Dimethyl-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,N-dimethyl-4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide (24.0 mg, 0.085 mmol) (may be prepared as described in Description 42) in dichloromethane (2 ml) was treated with 2-methylpropanal (16.0 μl, 0.17 mmol) and acetic acid (1 drop) and stirred at room temperature. Sodium triacetoxyborohydride (36.0 mg, 0.17 mmol) was added and the mixture was stirred at room temperature for approximately 50 hours. 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 (E1); MS (ES+) m/e 357 [M+NH3]+.

Workup

  1. stirringthe mixture was stirred at room temperature for approximately 50 hours
  2. washeluting with methanol
  3. customevaporated

Sources & evidence

ORD record
ord-898af5f6e78b47aab0e98453cf055c34
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

Loading…