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

HRID 1666097Notes

Reaction equation

HRID 1666097 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-e161d56555fd4443960c836a2f625f9a
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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