Triethylamine → HCID 86687858, compound

HRID 535906Notes

Reaction equation

HRID 535906 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(O[N:33]1N=[N:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:47](N(CC)CC)C>CN(C=O)C>[N:40]1[CH:35]=[CH:36][CH:37]=[C:38]([CH2:39][CH2:34][NH:33][C:20]([C:19]2[CH:18]=[CH:17][C:16]([CH2:15][N:12]3[CH2:13][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:10][CH2:11]3)=[CH:24][CH:23]=2)=[O:22])[CH:47]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 53256159HCID 53256159, compound

Product 1

HCID 86687858HCID 86687858, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[(4-{[(tert-butoxy)carbonyl]amino}piperidin-1-yl)methyl]benzoic acid (Intermediate XIII.1; 3.00 g; 8.97 mmol), TBTU (3.20 mg; 9.97 mmol) and triethylamine (1.40 ml; 10.0 mmol) in DMF (50 ml) is stirred for 5 min. The amine 3-(2-aminoethyl)-pyridine (1.06 ml; 9.00 mmol) is added. After further 3 h stirring, the solvent is evaporated and the residue is taken up in DCM and washed with sodium carbonate solution. The organic layer is dried over sodium sulphate, filtered and evaporated. The residue is purified by silica gel column chromatography (gradient DCM/Methanol) to yield tert-Butyl N-[1-({4-[(2-(3-pyridyl)-ethylamino)carbonyl]phenyl}methyl)piperidin-4-yl]carbamate

Workup

  1. stirringAfter further 3 h stirring
  2. customthe solvent is evaporated
  3. washwashed with sodium carbonate solution
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by silica gel column chromatography (gradient DCM/Methanol)

Sources & evidence

ORD record
ord-ea3e201ca06248c08d83f61ccf6f84cb
Source dataset
uspto-grants-2014_10
Patent number
US08859559B2

Reaction notes

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