Cyclohexanone → HCID 11533380, compound

HRID 734792Notes

Reaction equation

HRID 734792 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]#[C:36][C:37]3[CH:50]=[CH:49][C:40]([O:41][CH2:42][CH2:43][NH:44][CH2:45][CH:46]4[CH2:48][CH2:47]4)=[C:39]([CH3:51])[CH:38]=3)=[N:33][CH:34]=2)=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>CC(O)=O.C1COCC1.C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]#[C:36][C:37]3[CH:50]=[CH:49][C:40]([O:41][CH2:42][CH2:43][N:44]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:45][CH:46]4[CH2:48][CH2:47]4)=[C:39]([CH3:51])[CH:38]=3)=[N:33][CH:34]=2)=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 7967Cyclohexanone2×HCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 11538940HCID 11538940, compound

Product 1

HCID 11533380HCID 11533380, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

30 μL (0.29 mmol) of cyclohexanone, 1 drop of AcOH, and 128 mg (0.68 mmol) of sodium triacetoxyborohydride were added to a solution of 60 mg (0.14 mmol) of (2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethyl)cyclopropylmethylamine in 10 mL of THF and the mixture was stirred for 24 hours at RT. 5 mL of DCM, 30 μL (0.29 mmol) of cyclohexanone, and 36 mg (0.58 mmol) of sodium cyanoborohydride were added and the mixture was stirred for a further 3 days. The reaction mixture was evaporated down in vacuo and the residue was taken up in EtOAc. The organic phase was washed with semiconcentrated aqueous sodium bicarbonate solution, dried over sodium sulfate, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, cyc/EtOAc 1:1) and triturated with PE. Yield: 4.5 mg (6% of theoretical); C32H35ClN2O (M=499.086); calc.: molpeak (M+H)+: 499/501 (Cl); found: molpeak (M+H)+: 499/501 (Cl); HPLC-MS: 9.85 minutes (method A).

Workup

  1. stirringthe mixture was stirred for a further 3 days
  2. customThe reaction mixture was evaporated down in vacuo
  3. washThe organic phase was washed with semiconcentrated aqueous sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated down in vacuo
  6. customThe residue was purified by column chromatography (silica gel, cyc/EtOAc 1:1)
  7. customtriturated with PE
  8. custom9.85 minutes (method A)

Sources & evidence

ORD record
ord-71bb6304e8bb4bdfaff8ba23dc30ca8f
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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