4-Piperidinol, 1-methyl- → HCID 10228736, compound

HRID 852057Notes

Reaction equation

HRID 852057 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.CC(C)([O-])C.[K+].[CH3:15][C:16]([CH3:46])([CH3:45])[CH2:17][N:18]([CH3:44])[C:19]1[N:24]=[C:23](S(C)(=O)=O)[N:22]=[C:21]([NH:29][C:30]2[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=2[CH3:40])[C:33]([NH:35][CH3:36])=[O:34])[C:20]=1[N+:41]([O-:43])=[O:42]>CS(C)=O>[CH3:15][C:16]([CH3:46])([CH3:45])[CH2:17][N:18]([CH3:44])[C:19]1[N:24]=[C:23]([O:8][CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[N:22]=[C:21]([NH:29][C:30]2[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=2[CH3:40])[C:33]([NH:35][CH3:36])=[O:34])[C:20]=1[N+:41]([O-:43])=[O:42]

Participants

5

Reactant 3

HCID 660484-Piperidinol, 1-methyl-HCID 23665647Potassium tert-butoxideHCID 58928536HCID 58928536, compound

Product 1

HCID 10228736HCID 10228736, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1-Methyl-piperidin-4-ol (56 mg, 0.5 mmol) was dissolved in 2 mL of DMSO. To the solution was added potassium tert-butoxide (56 mg, 0.5 mmol). The solution was stirred at room temperature for 1 h. The solution was then added to a solution of 3-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-2-methanesulfonyl-5-nitro-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide (4 mg, 0.01 mmol) in 0.5 mL of DMSO. The solution was stirred at 80° C. for 3 h, and extracted with ethyl acetate and water. The organic layer was washed with water, brine, dried over MgSO4, and evaporated under vacuum. The residue was purified by semi-preparative hplc column to afford 0.7 mg of the product (Yield: 16%). MS (m/z) calcd for C25H37N7O4 (MH+), 500.2, found, 500.1.

Workup

  1. stirringThe solution was stirred at 80° C. for 3 h
  2. extractionextracted with ethyl acetate and water
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuum
  6. customThe residue was purified by semi-preparative hplc column

Sources & evidence

ORD record
ord-93f6c487055243189fe592651f255dce
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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