Triethylamine → HCID 89855035, compound

HRID 931256Notes

Reaction equation

HRID 931256 reaction equation
[F:1][C:2]1([F:13])[CH2:7][NH:6][CH2:5][CH:4]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:3]1.C(N(CC)CC)C.[NH2:21][C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24](Cl)[N:23]=1>CS(C)=O>[NH2:21][C:22]1[N:23]=[C:24]([N:6]2[CH2:7][C:2]([F:1])([F:13])[CH2:3][CH:4]([C:8]([N:10]([CH3:11])[CH3:12])=[O:9])[CH2:5]2)[CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 117966527HCID 117966527, compound

Product 1

HCID 89855035HCID 89855035, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5,5-difluoro-N,N-dimethylpiperidine-3-carboxamide (700 mg, 3.05 mmol) in dimethylsulfoxide (30 mL) were added triethylamine (619.2 mg, 6.11 mmol) and 2-amino-6-chloro-3-nitropyridine (531.1 mg, 3.059 mmol). The reaction mixture was heated to 100° C. After 16 h, the mixture was cooled to room temperature and was partitioned between ethyl acetate and water (2×). The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was triturated with pentane to afford 1-(6-amino-5-nitropyridin-2-yl)-5,5-difluoro-N,N-dimethylpiperidine-3-carboxamide (0.9 g) as a yellow solid. MS (ES+APCI) (M+H) 330.2; LCMS retention time: 3.066 min (Method U1).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. customwas partitioned between ethyl acetate and water (2×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was triturated with pentane

Sources & evidence

ORD record
ord-2b3a4bc72fc044b79254aa8fa8c23a5a
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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