HCID 10619851, compound → HCID 10761696, compound

HRID 361831Notes

Reaction equation

HRID 361831 reaction equation
C[Li].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:30])[C:17]2[C:22]([NH:23][C:24]([CH3:28])([C:26]#N)[CH3:25])=[CH:21][CH:20]=[C:19]([F:29])[N:18]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1(C)C=CC=CC=1>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:30])[C:17]2[C:22]([NH:23][C:24]([CH3:25])([CH3:26])[CH3:28])=[CH:21][CH:20]=[C:19]([F:29])[N:18]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 10619851HCID 10619851, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 10761696HCID 10761696, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methyllithium (53 ml, 74.2 mmol, 1.4M in ether) is added to toluene (15 ml) in a dry flask under a nitrogen atmosphere at -78°. 1-Benzyl-4-[N-methyl-N-(3-(1-methyl-1-cyanoethyl)amino-6-fluoro-2-pyridinyl)amino]piperidine (EXAMPLE 152, 2.83 g, 7.42 mmol) in toluene (15 ml) is cooled to -78° and cannulated into the methyllithium mixture. The mixture is allowed to warm gradually to 20°-25°, then quenched cautiously with water. The mixture is extracted with chloroform and the extract dried over sodium sulfate, filtered and concentrated. The concentrate is chromatography (silica gel, 100 g; ethyl acetate/hexane (20/80)) to give the title compound; NMR (300 MHz, CD3OD) 7.55, 7.48, 6.78, 3.68, 3.25, 3.10, 2.74, 2.20-2.30, 1.75-1.90 and 1.52δ.

Workup

  1. temperatureto warm gradually to 20°-25°
  2. customquenched cautiously with water
  3. extractionThe mixture is extracted with chloroform
  4. dry with materialthe extract dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-02843fc3c6c34574ab919d5228c2c7cd
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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