Triethylamine → HCID 66967018, compound

HRID 1362116Notes

Reaction equation

HRID 1362116 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)[CH3:2].C(N(CC)CC)C.Br.[Br:26][C:27]1[CH:28]=[C:29]([CH2:34]Br)[C:30]([NH2:33])=[N:31][CH:32]=1>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]([CH2:34][C:29]1[C:30]([NH2:33])=[N:31][CH:32]=[C:27]([Br:26])[CH:28]=1)[CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromideHCID 66967695HCID 66967695, compound

Product 1

HCID 66967018HCID 66967018, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of [3-(4-methyl-piperazin-1-yl)propylamino]acetic acid ethyl ester (1.80 g, 7.41 mmol) and triethylamine (2.3 mL, 16.4 mmol) in DMF (50 mL) was treated with 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (2.57 g, 7.41 mmol). After stirring at room temperature for 3 d, the mixture was diluted with H2O (100 mL) and then extracted with EtOAc (4×100 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 97:3 to 90:10) gave the title compound (0.50 g, 16%) as a colorless oil: MS (ESI) m/e 428 (M+H)+.

Workup

  1. extractionextracted with EtOAc (4×100 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 97:3 to 90:10)

Sources & evidence

ORD record
ord-753067e810544c1282339abac0e8e95a
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…