Triethylamine → (6-Chloro-[1,2,3]triazolo[4,5-b]pyridin-1-yl)-(4-methyl-piperidin-1-yl)-methanone

HRID 2237594Notes

Reaction equation

HRID 2237594 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:10][N:9]=[N:8][C:5]2=[N:6][CH:7]=1.[CH3:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18](Cl)=[O:19])[CH2:14][CH2:13]1.C(N(CC)CC)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([C:18]([N:15]3[CH2:16][CH2:17][CH:12]([CH3:11])[CH2:13][CH2:14]3)=[O:19])[N:9]=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152215164-Methylpiperidine-1-carbonyl ChlorideHCID 178478278HCID 178478278, compound

Product 1

HCID 59302801(6-Chloro-[1,2,3]triazolo[4,5-b]pyridin-1-yl)-(4-methyl-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-Chloro-1H-[1,2,3]triazolo[4,5-b]pyridine (200 mg, 1.29 mmol) and 4-methyl-piperidin-1-carbonyl chloride (418 mg, 2.56 mmol) were dissolved in 10 ml of pyridine. Then triethylamine (180 μl, 3.88 mmol) was added and stirred at room temperature for 4 h and left to stand overnight. The reaction mixture was concentrated and the residue was mixed with water and ethyl acetate. The organic phase was separated off, the aqueous phase was extracted once more, and the combined organic phases were washed with water and concentrated. The crude product was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 106 mg (29%) of (6-chloro-[1,2,3]triazolo[4,5-b]pyridin-1-yl)-(4-methyl-piperidin-1-yl)-methanone, M+H+: 280.2.

Workup

  1. waitleft
  2. waitto stand overnight
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was mixed with water and ethyl acetate
  5. customThe organic phase was separated off
  6. extractionthe aqueous phase was extracted once more
  7. washthe combined organic phases were washed with water
  8. concentrationconcentrated
  9. customThe crude product was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-2d78e0cb7a474852ad314e81a45b6dd7
Source dataset
uspto-grants-2010_05
Patent number
US07718669B2

Reaction notes

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