Methylamine → 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]-N-methylbutanamide

HRID 639829Notes

Reaction equation

HRID 639829 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:24])[CH2:20][C:21]([OH:23])=O)[N:18]=2)[CH:11]=[CH:12][CH:13]=1.[CH3:25][NH2:26].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:24])[CH2:20][C:21]([NH:26][CH3:25])=[O:23])[N:18]=2)[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 684316183-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butanoic acid

Product 1

HCID 684324593-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]-N-methylbutanamideYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalylchloride (2 mL, 3.9 mmol) was added during 5 minutes to 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butanoic acid in DCM (40 mL) and DMF (5 drops) under argon. The mixture was stirred at r.t. for 3 h and then was MeNH2 (2M in THF, 3.6 mL, 7.2 mmol) added and the resulting mixture was stirred o.n. Saturated NaHCO3 (75 mL) was added and the mixture was extracted with CHCl3 (3×100 mL). The combined organic phases were dried (MgSO4) and concentrated. The crude was purified by flash column chromatography (SiO2, Heptane-EtOAc 1:2) to give 0.74 g (74%) of the title compound.

Workup

  1. additionadded
  2. stirringthe resulting mixture was stirred o.n
  3. extractionthe mixture was extracted with CHCl3 (3×100 mL)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude was purified by flash column chromatography (SiO2, Heptane-EtOAc 1:2)

Sources & evidence

ORD record
ord-714cd48aca3f4814868601b71f9ed54c
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

Loading…