Water → Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6-chloroisonicotinate

HRID 2233822Notes

Reaction equation

HRID 2233822 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24](Cl)[N:25]=1)[C:19]([O:21][CH3:22])=[O:20].O.[Na+].[Cl-]>CN1C(=O)CCC1.CCOC(C)=O>[C:10]([O:9][C:8]([NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:24]2[CH:23]=[C:18]([CH:17]=[C:16]([Cl:15])[N:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 93237Methyl 2,6-dichloroisonicotinate2×HCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 86608242Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6-chloroisonicotinate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

tert-Butyl piperidin-4-ylcarbamate (972 mg, 4.85 mmol), was dissolved in anhydrous NMP (5 ml). Methyl 2,6-dichloroisonicotinate (Intermediate 24, 1 g, 4.85 mmol) was added followed by TEA (675 μl, 4.85 mmol). The mixture was heated under microwave conditions at 150° C. for 10 minutes. Water (50 ml) and EtOAc (100 ml) were added, the aqueous phase was treated with solid NaCl and extracted with EtOAc (4×100 ml). The EtOAc layer was dried, concentrated in vacuo and purified by flash chromatography eluting with hexane:EtOAc (4:1) to give the title product as an off-white solid. (1.4 g).

Workup

  1. extractionextracted with EtOAc (4×100 ml)
  2. dry with materialThe EtOAc layer was dried
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography
  5. washeluting with hexane:EtOAc (4:1)

Sources & evidence

ORD record
ord-0a67e466361e4db2977a5287212d5a6e
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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