Triethylamine → HCID 67434472, compound

HRID 1662990Notes

Reaction equation

HRID 1662990 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Cl.[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH2:20])[CH3:16].C(N(CC)CC)C.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH:20][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1)[CH3:16]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723640Glycine ethyl ester, hydrochlorideHCID 27764884-(1H-1,2,4-triazol-1-yl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 67434472HCID 67434472, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.5 g (20 mmol) of 4-[1,2,4]triazol-1-yl-benzaldehyde and 4.19 g (30 mmol) of glycine ethyl ester hydrochloride in 100 ml of CH2Cl2, 4.18 ml (30 mmol) of triethyl amine and excess of MgSO4 (14 g) are successively added at r.t. After being stirred for 18 h at r.t., the reaction mixture is filtered through celite and concentrated under reduced pressure. The residue is diluted with AcOEt and filtered again. The filtrate is concentrated under reduced pressure to give the crude imine. To a solution of the crude imine in 12 ml of MeOH, 0.756 mg (20 mmol) of NaBH4 is added at −10° C. After being stirred for 1 h, the reaction is quenched with sat. NH4Cl and the reaction mixture is extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: n-Hexane:AcOEt=1:10) to give the title compound. 1H-NMR (400 MHz, CDCl3): 1.29 (t, 3H, J=7.04 Hz), 1.90 (brs, 1H), 3.43 (s, 2H), 3.88 (s, 2H), 4.21 (q, 2H, J=7.04 Hz), 7.49 (d, 2H, J=8.56 Hz), 7.64 (d, 2H, J=8.56 Hz), 8.10 (s, 1H), 8.55 (s, 1H).

Workup

  1. filtrationthe reaction mixture is filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is diluted with AcOEt
  4. filtrationfiltered again
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customto give the crude imine
  7. stirringAfter being stirred for 1 h
  8. customthe reaction is quenched with sat. NH4Cl
  9. extractionthe reaction mixture is extracted with AcOEt
  10. washThe combined extracts are washed with brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under reduced pressure
  13. customThe residue is purified by column chromatography on silica gel (eluent: n-Hexane:AcOEt=1:10)

Sources & evidence

ORD record
ord-962173be86bf47c894b7ae5e1fe5c087
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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