Dimethylformamide → [5-(4-Ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl ester

HRID 43066Notes

Reaction equation

HRID 43066 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15]OS(C)(=O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>CCOC(C)=O.O.CCOCC>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:26]2[CH2:27][CH2:28][N:23]([CH2:21][CH3:22])[CH2:24][CH2:25]2)=[CH:13][N:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 791961-EthylpiperazineHCID 86641141(6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonate

Product 1

HCID 66914627[5-(4-Ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl esterYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methanesulfonic acid 6-tert-butoxycarbonylamino-pyridin-3-ylmethyl ester (Step 26.3) (0.8 g, 2.6 mmol), N-ethylpiperazine (0.37 mL, 2.9 mmol, 1.1 equiv), cesium carbonate (1 g, 3.2 mmol, 1.2 equiv), and DMF (10 ml) was stirred for 2 h at rt, diluted with EtOAc and H2O, and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to provide a yellow solid. Trituration in Et2O afforded 0.75 g of the title compound as a white solid: ES-MS: 321.2 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a yellow solid

Sources & evidence

ORD record
ord-67ab2e417bfa4908aed9eb3b06809570
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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