Triethylamine → HCID 178512295, compound

HRID 1383451Notes

Reaction equation

HRID 1383451 reaction equation
[C:1]([NH:3][C:4]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)#[N:2].Br[CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH:22]([N:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][NH:12][C:4]([NH:3][C:1]#[N:2])=[N:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH2:20][CH2:19]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 236603BromodiphenylmethaneHCID 178512294HCID 178512294, compound

Product 1

HCID 178512295HCID 178512295, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-cyano-N′-(2-piperazin-1-yl-ethyl)-N″-pyridin-4-yl-guanidine (273 mg, 1 mmol) (prepared using the procedure described in Example 7) and bromodiphenylmethane (247 mg, 1 mmol) was dissolved in dimethylformamide (1.5 mL), followed by the addition of triethylamine (0.21 mL, 1.5 mmol). The reaction solution was stirred at room temperature under nitrogen for 10-15 hours and then diluted with 100 mL ethyl acetate. The organic layer was washed with water (3×30 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give crude title product. The final product was further purified by flash column chromatography (SiO2, 10% MeOH in EtOAc). The pure product was obtained in 50% yield in two steps. 1H-NMR (CD3OD, ppm): 8.36 (d, 2H), 7.18-7.43 (m, 12H), 4.29 (s, 1H), 3.46 (t, 2H), 2.45-2.61 (m, 10H). ESMS 440.4 (M+1), 462.4 (M+23).

Workup

  1. washThe organic layer was washed with water (3×30 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b37c1432cbb04cc4b024ccdf46a7a7e4
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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