Carbonic acid, bis(1,1-dimethylethyl) ester → Tert-butyl 4-((6-aminopyridin-2-yl)methyl)piperazine-1-carboxylate

HRID 520485Notes

Reaction equation

HRID 520485 reaction equation
[N:1]1([CH2:7][C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:15](=O)([O:21]C(C)(C)C)[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]>C1COCC1.CN(C)C1C=CN=CC=1>[NH2:14][C:12]1[N:13]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][N:4]([C:15]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:21])[CH2:3][CH2:2]2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 585528446-(Piperazin-1-ylmethyl)picolinonitrile

Product 1

HCID 58552896Tert-butyl 4-((6-aminopyridin-2-yl)methyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(piperazin-1-ylmethyl)pyridin-2-amine 85 in THF was added di-tert-butyl carbonate (1 eq) and 4-(dimethyl)aminopyridine (catalytic). The reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. Pentane was added and the resulting solid was collected by filtration and dried to afford 86. The Boc protecting group could be removed after coupling with the appropriate carboxylic acid by treatment with TFA/CH2Cl2 for 12 h.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. additionPentane was added
  3. filtrationthe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-5882411819754903bf2a6cd903d258c2
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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