Sodium Bicarbonate → Tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate

HRID 2093436Notes

Reaction equation

HRID 2093436 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)=[C:2]=[O:3].C([O-])(O)=O.[Na+].[NH2:16][C:17]1[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=1)[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1>CCOC(C)=O>[CH3:10][C:7]1[N:8]=[CH:9][C:4]([NH:1][C:2](=[O:3])[NH:16][C:17]2[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=2)[CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:26][CH2:27]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 73305055-Isocyanato-2-methylpyridineHCID 57597088Tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate2×

Product 1

HCID 57597105Tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant provided tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate (7E, 63%).

Workup

  1. customThe resulting reaction mixture
  2. customthe layers were separated
  3. washThe organic layer was washed twice with saturated aq. NaHCO3 and once with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant

Sources & evidence

ORD record
ord-fdba80a0c137483a8239af8685e33b76
Source dataset
uspto-grants-2013_05
Patent number
US08445495B2

Reaction notes

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