Acetone → HCID 16048757, compound

HRID 1364144Notes

Reaction equation

HRID 1364144 reaction equation
[N:1]1[N:2]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])=[CH:13][CH:12]=2)[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=12.[CH3:23][C:24]([CH3:26])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH3:23][CH:24]([N:8]1[CH2:9][CH2:10][C:4]2=[CH:3][N:2]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:21][CH2:20][CH2:19][C:18]4=[O:22])=[CH:15][CH:16]=3)[N:1]=[C:5]2[CH2:6][CH2:7]1)[CH3:26]

Participants

7

Reactant 3

HCID 180Acetone2×HCID 5049666Sodium triacetoxyborohydride2×HCID 66930837HCID 66930837, compound

Product 1

HCID 16048757HCID 16048757, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)phenyl]-2-pyrrolidinone (may be prepared as described in Description 22) (45 mg, 0.15 mmol) in dichloromethane (3 ml) was added acetone (17 mg, 0.30 mmol) and acetic acid (2 drops). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added and stirring continued for 22 hours. A further 2 eq. of acetone (17 mg, 0.30 mmol) was added, and after a further 20 minutes a further 2 eq. of sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added and stirring continued for 3 hours. The resulting crude mixture was diluted with methanol and then purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo. Crude product was triturated with ether, filtered then triturated with ethyl acetate to afford the title compound (E14). MS (ES+) m/e 339 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 22 hours
  3. stirringstirring
  4. waitcontinued for 3 hours
  5. custompurified by SCX
  6. washeluting with methanol
  7. customsolvent evaporated in vacuo
  8. customCrude product was triturated with ether
  9. filtrationfiltered
  10. customthen triturated with ethyl acetate

Sources & evidence

ORD record
ord-eec51f4bc6984039ad6588f20cc621b7
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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