Water → tert-Butyl 1-[4-(aminocarbonyl)-6-chloropyridin-2-yl]piperidin-4-ylcarbamate

HRID 2233818Notes

Reaction equation

HRID 2233818 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:22]=[C:23](Cl)[N:24]=1)[C:19]([NH2:21])=[O:20].CN(C(C(C)C)C)C.O>CCOC(C)=O>[NH2:21][C:19]([C:18]1[CH:17]=[C:16]([Cl:15])[N:24]=[C:23]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)[CH:22]=1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7238334-(N-Boc-amino)piperidineHCID 27818022,6-DichloroisonicotinamideHCID 22949790N,N,3-Trimethylbutan-2-amine

Product 1

HCID 86608240tert-Butyl 1-[4-(aminocarbonyl)-6-chloropyridin-2-yl]piperidin-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl piperidin-4-ylcarbamate (500 mg, 2.62 mmol), was dissolved in anhydrous N,N′-dimethyl acetamide (4 ml). 2,6-Dichloroisonicotinamide (522 mg, 2.62 mmol) was added, followed by N,N-dimethyl isopropylethylamine (465 μl, 2.62 mmol). Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 20 minutes. H2O (50 ml) and EtOAc (100 ml) were added, the EtOAc layer was washed (4×50 ml), dried over Na2SO4 and concentrated in vacuo to give the title product as a brown solid. (760 mg).

Workup

  1. customat 150° C.
  2. customfor 20 minutes
  3. washthe EtOAc layer was washed (4×50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-933431a950fd470aab564864844c2919
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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