Pyridine → HCID 59394204, compound

HRID 884524Notes

Reaction equation

HRID 884524 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1.N1C=CC=CC=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C1COCC1.C(Cl)Cl>[C:22]1([O:21][C:19](=[O:20])[NH:9][C:5]2[CH:6]=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 140519365-(Trifluoromethyl)pyridin-3-amine

Product 1

HCID 59394204HCID 59394204, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Example 7-A, 5-trifluoromethyl-pyridin-3-ylamine, (385 mg, 2.37 mmol) is taken up in THF (25 mL) and pyridine (0.38 mL, 4.75 mmol) at 0° C. before phenyl chloroformate (558 mg, 3.56 mmol) is added. After 2 h, the reaction is diluted with DCM (50 mL) and washed with water (50 mL). The organic layer is separated, dried over anhydrous Na2SO4, filtered and concentrated. The residue is then separated via FCC (EtOAc/heptanes 1:9 to EtOAc/heptanes 1:1) to give the title compound. MS (ESI) m/z 283.0 (M+1).

Workup

  1. washwashed with water (50 mL)
  2. customThe organic layer is separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is then separated via FCC (EtOAc/heptanes 1:9 to EtOAc/heptanes 1:1)

Sources & evidence

ORD record
ord-6c2fb6627cdb47aaaa682a35af9f0251
Source dataset
uspto-grants-2012_08
Patent number
US08242125B2

Reaction notes

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