Diisopropylethylamine → Methyl 6-[4-[[(1,1-dimethylethoxy)carbonyl]amino]-1-piperidinyl]-3-pyridinecarboxylate

HRID 1486815Notes

Reaction equation

HRID 1486815 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[C:12]([NH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[C:15]([O:14][C:12]([NH:19][CH:20]1[CH2:21][CH2:22][N:23]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=2)[CH2:24][CH2:25]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 90418825Methyl 6-[4-[[(1,1-dimethylethoxy)carbonyl]amino]-1-piperidinyl]-3-pyridinecarboxylateYield 84.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 6-chloropyridine-3-carboxylate (1.00 g, 5.83 mmol) and 4-(N-Boc-amino)piperidine (2.33 g, 11.7 mmol) were dissolved in DMF (10 mL) and the reaction mixture was heated using a microwave reactor at 100° C. for 50 min. DIPEA (1.22 mL, 6.99 mmol) was added and the reaction mixture was heated using a microwave reactor at 100° C. for 30 min. The reaction mixture was diluted with DCM (50 mL), washed with sat aq NaHCO3 (2×50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (1.66 g, 84.9%) as an off-white solid. LCMS (ES+): 336.1 [MH]+. HPLC: Rt 4.73 min, 98.2% purity.

Workup

  1. temperaturethe reaction mixture was heated
  2. customat 100° C.
  3. customfor 50 min
  4. temperaturethe reaction mixture was heated
  5. customat 100° C.
  6. customfor 30 min
  7. washwashed with sat aq NaHCO3 (2×50 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5e873720265f4a6da370a2195dd9df5a
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

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