Triethylamine → HCID 86761877, compound

HRID 1527895Notes

Reaction equation

HRID 1527895 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Br)=[C:14]([Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:13]=1)[Si](C)(C)C)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([CH2:18][C:15]2[CH:16]=[CH:17][C:12]([NH:7][C:6](=[O:24])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13][C:14]=2[Si:20]([CH3:23])([CH3:22])[CH3:21])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 86632316HCID 86632316, compound

Product 1

HCID 86761877HCID 86761877, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude tert-butyl(4-bromomethyl-3-trimethylsilylphenyl)trimethylsilylcarbamate (2.57 g, 5.98 mmol) in THF (10 mL) was added Et3N (1.3 mL, 8.97 mmol) and 1-methylpiperazine (1.1 mL, 8.92 mmol). After stirring for 1 h at rt, aq. NaHCO3 was added, and the mixture was extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluted with 5% MeOH/DCM) to provide product as a pale yellow oil (1.60 g, 71%).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe resulting residue was purified by silica gel chromatography (eluted with 5% MeOH/DCM)

Sources & evidence

ORD record
ord-b03c9a3adaf74754818a9ee0d235779e
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

Loading…