Acetone → HCID 16048760, compound

HRID 1364147Notes

Reaction equation

HRID 1364147 reaction equation
[N:1]1[N:2]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=2)[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=12.[CH3:20][C:21]([CH3:23])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl.C(O)(=O)C>[CH3:20][CH:21]([N:8]1[CH2:9][CH2:10][C:4]2=[CH:3][N:2]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=3)[N:1]=[C:5]2[CH2:6][CH2:7]1)[CH3:23]

Participants

7

Reactant 4

HCID 180Acetone2×HCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 66930841HCID 66930841, compound

Product 1

HCID 16048760HCID 16048760, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide (may be prepared as described in Description 37) (31 mg, 0.12 mmol) in dichloromethane (3 ml) was added acetone (14 mg, 0.24 mmol) and acetic acid (2 drops). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (51 mg, 0.24 mmol) was added and stirring continued for 2 hours. A further 6 eq. of acetone was added and stirring continued over the weekend. Methanol was added and the crude mixture was purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo. The crude product was triturated with ether and filtered to afford the title compound (E17). MS (ES+) m/e 299 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. stirringstirring
  4. customthe crude mixture was purified by SCX
  5. washeluting with methanol
  6. customsolvent evaporated in vacuo
  7. customThe crude product was triturated with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-41e1641ff4f440708466c32eaf8dc53a
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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