4-(N-Boc-amino)piperidine → HCID 86608254, compound

HRID 2233860Notes

Reaction equation

HRID 2233860 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]1>CN1C(=O)CCC1>[C:11]([NH:10][C:4]1[N:5]=[C:6]([S:8][CH3:9])[N:7]=[C:2]([N:14]2[CH2:15][CH2:16][CH:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:18][CH2:19]2)[CH:3]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7238334-(N-Boc-amino)piperidineHCID 13447564N-[6-Chloro-2-(methylsulfanyl)pyrimidin-4-yl]acetamide2×

Product 1

HCID 86608254HCID 86608254, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

TEA (0.32 ml, 2.28 mmol) and N-[6-chloro-2-(methylthio)pyrimidin-4-yl]acetamide (Intermediate 44, 0.50 g, 2.28 mmol) were added to a solution of tert-butyl piperidin-4-ylcarbamate (0.46 g, 2.28 mmol) in NMP (2 ml) at room temperature. Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 10 minutes. The mixture was partitioned between water and EtOAc. The layers were separated and the organic layer was washed with water two more times. The organic phase was dried over magnesium sulfate and concentrated to give the title compound (816 mg).

Workup

  1. customat 150° C.
  2. customfor 10 minutes
  3. customThe mixture was partitioned between water and EtOAc
  4. customThe layers were separated
  5. washthe organic layer was washed with water two more times
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aea0fc5df0d64898b667f0ef62ea0015
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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