Triethylamine → HCID 66967252, compound

HRID 1711852Notes

Reaction equation

HRID 1711852 reaction equation
C(O[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)C.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>[Br:26][C:27]1[CH:32]=[N:31][C:30]2[NH:33][C:4](=[O:17])[CH2:5][N:6]([CH2:7][CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)[CH2:34][C:29]=2[CH:28]=1

Participants

6

Reactant 3

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

Product 1

HCID 66967252HCID 66967252, compoundYield 17.7%

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-cc6ce7b9a2834db6a9ebddd5f470c2d7
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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