Triethylamine → HCID 178497766, compound

HRID 77512Notes

Reaction equation

HRID 77512 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[NH:14])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.C(N(CC)CC)C.[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]Br)[CH:33]=1>CN(C=O)C>[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][N:18]2[CH2:19][CH2:20][CH2:21][C@H:16]([NH:15][C:13]([NH2:14])=[N:12][C:10]([C:3]3[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=3)=[O:11])[CH2:17]2)[CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 178512392N-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-N'-piperidin-3-yl-guanidine

Product 1

HCID 178497766HCID 178497766, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.17 g (4.5 mmol) 4-Aminomethyl-4-phenethyl-piperidine-1-carbocylic acid tert-butyl ester (intermediate 3), 1 mg (4.9 mmol) (S)-3-amino-piperidine-1-carboxylic acid tert-butyl ester and 125 μl triethylamin in 50 ml DMF/iso-propanol (1:3) is stirred at 70° C. overnight. Then the reaction mixture is concentrated under reduced pressure. Then 50 ml 25% TFA in dicholoromethane is added and the mixture is stirred for 2 h at room temperature and evaporated. The residue is treated with excess HCl in methanol and evaporated again to yield 430 mg N-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-N′-piperidin-3-yl-guanidine. Step B: 100 mg N-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-N′-piperidin-3-yl-guanidine, 125 μl triethylamine and 62 mg 3-bromomethyl-benzoic acid methyl ester in 3 ml DMF were stirred at room temperature for 6 h. Then the reaction mixture is concentrated under reduced pressure and the residue is purified by preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.). Fractions containing the title compound were concentrated under reduced pressure.

Workup

  1. concentrationThen the reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified by preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.)
  3. additionFractions containing the title compound
  4. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-7fd2f4caf0df49348df43f0227d30dc4
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Reaction notes

Loading…