4-Piperidinemethanol → [1-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-yl]-methanol

HRID 2285013Notes

Reaction equation

HRID 2285013 reaction equation
Cl[C:2]1[N:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1>CN1C(=O)CCC1>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]3)=[N:3][N:4]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4207714-PiperidinemethanolHCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 86687044[1-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-yl]-methanolYield 56%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of Intermediate 24b (593 mg, 3.45 mmol) and 4-piperidinemethanol (1.59 g, 13.8 mmol) in NMP (10 mL) was heated in the microwave at 170° C. for 3 h. The cooled mixture was applied to an SCX-2 cartridge (70 g), washing with methanol then eluting basic components with 0.4 2 M NH3 in MeOH. Product containing fractions were combined and concentrated in vacuo. The residue was purified by FCC, using 0-15% MeOH in EtOAc, to give the title compound as a brown gum (481 mg, 56%). LCMS (Method 3): Rt 2.12 min, m/z 251 [MH+].

Workup

  1. washwashing with methanol
  2. washthen eluting basic components with 0.4 2 M NH3 in MeOH
  3. additionProduct containing fractions
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-9f98bb12aae643839a179acf26020fa3
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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