Methanol → HCID 86687094, compound

HRID 1402240Notes

Reaction equation

HRID 1402240 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.[CH3:12][OH:13]>CC(N(C)C)=O.C(Cl)Cl>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([N:6]3[CH2:7][CH2:8][CH2:9][C@@H:10]([CH2:12][OH:13])[CH2:5]3)=[N:3][N:4]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 86687094HCID 86687094, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

A brown solution of Intermediate 24b (565 mg, 3.29 mmol) and R-3-hydroxymethyl piperidine (Chess GmbH, 948 mg, 8.23 mmol) in DMA (10 mL) was irradiated at 175° C. for 3 h in the microwave. The cooled solution was concentrated in vacuo, suspended in water (10 mL) and brine (10 mL), and then extracted with DCM (2×20 mL). The combined organics were passed through a hydrophobic frit and concentrated in vacuo to leave a brown oil. FCC, using 4-5% MeOH in DCM, gave the title compound as a viscous yellow oil (237 mg, 29%). LCMS (Method 3): Rt 2.11 min, m/z 251 [MH+].

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. extractionbrine (10 mL), and then extracted with DCM (2×20 mL)
  3. concentrationconcentrated in vacuo
  4. customto leave a brown oil

Sources & evidence

ORD record
ord-180bdae737114d21b55747998c8c9d65
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…