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

HRID 1402217Notes

Reaction equation

HRID 1402217 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][CH2:19]O)[CH2:14][CH2:13]1.CC(N(C)C)=[O:23]>>[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]([CH:18]([OH:23])[CH3:19])[CH2:14][CH2:13]3)=[N:3][N:4]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 739534-PiperidineethanolHCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 86687072[1-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-yl]-ethanolYield 41%

Conditions

Temperature
170 °C

Procedure

A mixture of Intermediate 24b (542 mg, 3.17 mmol) and 4-piperidine-ethanol (1.54 g, 11.9 mmol) in DMA (10 mL) was heated in the microwave at 170° C. for 3 h. The cooled mixture was applied to an SCX-2 cartridge (50 g), washing with methanol then eluting basic components with 0.4-2 M ammonia in methanol. Product containing fractions were combined and concentrated in vacuo. The residue was purified by FCC, using 0-20% MeOH in DCM, to give the title compound as a pale brown solid (324 mg, 41%). LCMS (Method 3): Rt 2.28 min, m/z 265 [MH+].

Workup

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

Sources & evidence

ORD record
ord-c5b55e414a954433a826b6a72674c70a
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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