Triethylamine → HCID 86726887, compound

HRID 924436Notes

Reaction equation

HRID 924436 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13]1.C(N(CC)CC)C>C(O)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:13]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 122757652,4-Dichloro-5-nitropyridine

Product 1

HCID 86726887HCID 86726887, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,4-dichloro-5-nitropyridine (from AstaTech, 0.500 g, 2.59 mmol), tert-butyl (3S)-piperidin-3-ylcarbamate (0.52 g, 2.6 mmol) and triethylamine (1.1 mL, 7.9 mmol) in isopropyl alcohol (10 mL) was heated at 65° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was re-dissolved in EtOAc (40 mL) and washed with saturated aq. NaHCO3 and water (3×3 mL). The combined aqueous phases were extracted with EtOAc (3 mL). The combined organic layers were washed with brine (3 mL), then dried over Na2SO4, filtered and concentrated under reduced pressure to afford the sub-title compound (0.99 g), which was used in the subsequent reaction without further purification. LCMS (ESI) calc. for C15H22ClN4O4[M+H]+: m/z=357.1. found 357.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was re-dissolved in EtOAc (40 mL)
  3. washwashed with saturated aq. NaHCO3 and water (3×3 mL)
  4. extractionThe combined aqueous phases were extracted with EtOAc (3 mL)
  5. washThe combined organic layers were washed with brine (3 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4adcb13ed7284e308d5fb5c500abff18
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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