Triethylamine → HCID 11550193, compound

HRID 888660Notes

Reaction equation

HRID 888660 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](O)=[O:6].ON1C2C=CC=CC=2N=N1.Cl.[CH3:23][NH:24][O:25][CH3:26].C(N(CC)CC)C.CNC(N=C=NCC)CCNC>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([N:24]([O:25][CH3:26])[CH3:23])=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1012653,5-Difluorobenzoic acidHCID 230638731,3-Dimethylaminopropyl-3-ethylcarbodiimide

Product 1

HCID 11550193HCID 11550193, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cooled mixture of 3,5 difluoro benzoic acid (2.0 g, 0.012 mol), 1-hydroxy-benzotriazole (HOBT, 2.5 g, 0.018 mol) and N,O-dimethylhydroxylamine HCl (2.35 g, 0.025 mol) in CH2Cl2(100 mL) was added triethylamine (5.0 mL, 0.036 mol) and followed by addition of 1,3-dimethylamino propyl-3-ethylcarbodiimide (EDC, 3.8 g, 0.019 mol). The mixture was allowed to warm to room temperature and continuously stir overnight. The reaction mixture was added EtOAc (300 mL) and then washed by diluted HCl solution, NaHCO3 and NaCl solution. The organic layer was collected and dried with Mg2SO4 and evaporated. The crude product was purified by column (0-50% EtOAc/Heptane) to give the title compound, 2.6 gm colorless oil. (100%)

Workup

  1. washwashed by diluted HCl solution, NaHCO3 and NaCl solution
  2. customThe organic layer was collected
  3. dry with materialdried with Mg2SO4
  4. customevaporated
  5. customThe crude product was purified by column (0-50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-48b3c9593fe04f93bd05d87439d3dbde
Source dataset
uspto-grants-2012_08
Patent number
US08247610B2

Reaction notes

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