Pyrrolidine → HCID 86687090, compound

HRID 1402236Notes

Reaction equation

HRID 1402236 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[CH2:16][CH2:15][CH2:14][CH2:13]1>CC(N(C)C)=O>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[N:3][N:4]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 86687090HCID 86687090, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of Intermediate 24b (515 mg, 3.00 mmol), pyrrolidine (0.85 g, 12.0 mmol) and DMA (10 mL) was heated to 175° C. for 4 h using microwave irradiation. After cooling, the solvent was removed in vacuo and the resulting residue purified by FCC, using 0 to 15% MeOH in DCM, to provide the title compound as a brown gum (285 mg, 26%). LCMS (Method 3): Rt 1.95 min, m/z 207 [MH+].

Workup

  1. custommicrowave irradiation
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. customthe resulting residue purified by FCC

Sources & evidence

ORD record
ord-d762e1cae4534a38a8d2bb757de38f73
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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