Triethylamine → HCID 67457252, compound

HRID 639646Notes

Reaction equation

HRID 639646 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]=[C:11]([CH2:26][CH2:27][OH:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29](N(CC)CC)C.CS(Cl)(=O)=O.S([O-])(=O)(=O)C.C[O-].[Na+]>ClCCl.CC(C)=O>[CH2:19]([NH:18][C:13]1[C:14]([N+:15]([O-:17])=[O:16])=[C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=[C:11]([CH2:26][CH2:27][O:28][CH3:29])[N:12]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 10942334Sodium MethoxideHCID 67455110HCID 67455110, compound

Product 1

HCID 67457252HCID 67457252, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

2-(4,6-Bis-benzylamino-5-nitro-pyridin-2-yl)-ethanol (134 mg, 35 mmol), was suspended in a mixture of dichloromethane (15 ml) and triethylamine (59 μl, 0.43 mmol) and the solution cooled to 5° C. in an ice bath. Methanesulphonyl chloride (33 μl, 0.43 mmol) was added and the reaction mixture stirred at ambient temperature for 1 h. A further 10 ml DCM was added, the organics washed with 2×K2CO3 (10% aq solution), dried and concentrated to afford a crude oil. The intermediate mesylate was suspended in acetone (20 ml) and sodium methoxide added (96 mg, 1.7 mmol), heating the mixture at reflux for 1 h. Residual solvent was removed in vacuo, DCM added and the solution washed with 2×H2O. The combined organics were dried over MgSO4, concentrated and purified by column chromatography on silica, eluting with Pent:EtOAc, 8:1 to 4:1 to afford the title compound as a yellow oil, (68 mg, 47%).

Workup

  1. washthe organics washed with 2×K2CO3 (10% aq solution)
  2. customdried
  3. concentrationconcentrated
  4. customto afford a crude oil
  5. temperatureheating the mixture
  6. temperatureat reflux for 1 h
  7. customResidual solvent was removed in vacuo, DCM
  8. additionadded
  9. washthe solution washed with 2×H2O
  10. dry with materialThe combined organics were dried over MgSO4
  11. concentrationconcentrated
  12. custompurified by column chromatography on silica
  13. washeluting with Pent

Sources & evidence

ORD record
ord-3566f0793c2c44c7abfb122bd0960e2e
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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