Ethyl bromoacetate → HCID 57861289, compound

HRID 1960022Notes

Reaction equation

HRID 1960022 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.BrCC([O:11][CH2:12][CH3:13])=O.C([O-])([O-])=O.[Cs+].[Cs+].[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH:25]=O.[BH4-].[Na+].[NH4+].[Cl-]>C(#N)C.C1(C)C=CC=CC=1.O.CCO>[F:20][C:21]([F:34])([F:35])[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:29]=1)[CH2:25][NH:1][C:2]1[N:3]=[N:4][N:5]([CH2:13][CH2:12][OH:11])[N:6]=1

Participants

11

Reactant 6

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydrideHCID 178509299HCID 178509299, compound

Product 1

HCID 57861289HCID 57861289, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-aminotetrazole (10.0 g, 0.12 mol), ethyl bromoacetate (20.0 g, 0.12 mol), and Cs2CO3 (40.0 g, 0.13 mol) in acetonitrile (220 mL) is stirred and refluxed for 5 hours. The mixture is cooled to 50° C. and filtrated. The resulting filtrate is concentrated to give the crude coupling product. The mixture of the crude product and 3,5-bis(trifluoromethyl)benzaldehyde (25.0 g, 0.10 mol) in toluene (220 mL) is stirred and refluxed for 5 hours. After cooling to room temperature, the resulting mixture is concentrated. NaBH4 (4.4 g, 0.12 mol) is added portionwise slowly to EtOH (220 mL) solution of the resulting residue, and the mixture is stirred at room temperature for 2 days. After addition of sat. NH4Cl aq. and water, the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give 2-(5-{N-[3,5-bis(trifluoromethyl)benzyl]amino}tetrazol-2-yl)ethanol.

Workup

  1. temperaturerefluxed for 5 hours
  2. filtrationfiltrated
  3. concentrationThe resulting filtrate is concentrated
  4. customto give the crude coupling product
  5. stirringis stirred
  6. temperaturerefluxed for 5 hours
  7. temperatureAfter cooling to room temperature
  8. concentrationthe resulting mixture is concentrated
  9. stirringthe mixture is stirred at room temperature for 2 days
  10. extractionthe mixture is extracted with ethyl acetate
  11. washThe combined organic layer is washed with brine
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-36559bfeb81c4116919ead21ce7b836d
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

Loading…