Hexachloroethane → (6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-dimethyl-amine

HRID 2285030Notes

Reaction equation

HRID 2285030 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10]([N:12]([CH3:14])[CH3:13])=O)=[N:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([N:12]([CH3:14])[CH3:13])=[N:9][N:8]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 866870622-(5-Fluoropyridin-2-yl)-N,N-dimethylhydrazine carboxamide

Product 1

HCID 86687063(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-dimethyl-amineYield 14.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Intermediate 59a (590 mg, 2.98 mmol), Ph3P (1.56 g, 5.96 mmol) and Et3N (1.20 g, 11.9 mmol) in THF (40 mL) was added hexachloroethane (1.41 g, 5.96 mmol) and the mixture stirred at 60° C. for 9 h. The mixture was diluted with EtOAc (100 mL), washed with water, brine, dried (MgSO4) and then concentrated in vacuo. The residue was purified by FCC, using 0-10% (2M NH3 in MeOH) in DCM, then triturated with diethyl ether to give the title compound (78 mg, 14%). LCMS (Method 1): Rt 2.24 min, m/z 181 [MH+].

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-f61f24b1fb0a4aab995daabde75d237e
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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