Triethylamine → HCID 67958117, compound

HRID 72447Notes

Reaction equation

HRID 72447 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[CH:9]2[CH2:12][NH:11][CH2:10]2)=[C:4]([CH3:14])[CH:3]=1.C(N(CC)CC)C.Cl[C:23]1[N:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]>O1CCCC1.CO>[Cl:33][C:30]1[CH:31]=[N:32][C:23]([N:11]2[CH2:12][CH:9]([N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[CH3:14])[CH3:13])[CH2:10]2)=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2764318Methyl 2,5-DichloronicotinateHCID 67958130N-(4-fluoro-2-methylphenyl)-N-methylazetidin-3-amine

Product 1

HCID 67958117HCID 67958117, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To mixture of N-methyl-N-(2-methyl-4-fluoro-phenyl)azetidin-3-amine (D56) (110 mg, 0.566 mmol) and triethylamine (0.18 ml, 0.849 mmol) in tetrahydrofuran/methanol (3/1 ml) Methyl 2,5-dichloronicotinate (116.82 mg, 0.566 mmol) was added and the mixture was heated at 75° C. for 12 hours. Solvents were evaporated and the residue was purified by SNAP-Si cartridge (10 g) eluting with cyclohexane/ethyl acetate from 100/0 to 90/10. Collected fractions after solvent evaporation afforded the title compound (D87) (170 mg)

Workup

  1. additionwas added
  2. customSolvents were evaporated
  3. customthe residue was purified by SNAP-Si cartridge (10 g)
  4. washeluting with cyclohexane/ethyl acetate from 100/0 to 90/10
  5. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-efac3eedf6114136b788bc6f5ce8dfd4
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

Loading…