Cyclohexanone → HCID 16048831, compound

HRID 1364151Notes

Reaction equation

HRID 1364151 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.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:23]1([N:8]2[CH2:9][CH2:10][C:4]3=[CH:3][N:2]([C:11]4[CH:12]=[CH:13][C:14]([N:17]5[CH2:21][CH2:20][CH2:19][C:18]5=[O:22])=[CH:15][CH:16]=4)[N:1]=[C:5]3[CH2:6][CH2:7]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 7967Cyclohexanone2×HCID 5049666Sodium triacetoxyborohydride2×HCID 66930837HCID 66930837, compound

Product 1

HCID 16048831HCID 16048831, 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 cyclohexanone (29 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 cyclohexanone (29 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 to afford the title compound (E22). MS (ES+) m/e 379 [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

Sources & evidence

ORD record
ord-3a8c2b08f7fb45e18f6ae20c50a11c79
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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