Triethylamine → HCID 178502677, compound

HRID 1022131Notes

Reaction equation

HRID 1022131 reaction equation
[N+:1]([C:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[NH:6][N:5]=1)([O-:3])=[O:2].Cl.[CH3:13][NH:14][O:15][CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl>[CH3:16][O:15][N:14]([CH3:13])[C:9]([C:7]1[NH:6][N:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=1)=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524578HCID 178524578, compound

Product 1

HCID 178502677HCID 178502677, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 3-nitro-1H-pyrazole-5-carboxylic acid (15.7 g, 1.0 eq., 100 mmol), N,O-dimethylhydroxylamine hydrochloride (19.5 g, 2.0 eq., 200 mmol), HATU (76.0 g, 2.0 eq., 200 mmol), triethylamine (40.4 g, 4.0 eq., 400 mmol), and dichloromethane (300 mL). The reaction mixture was stirred at room temperature for overnight. The solvent was removed under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 287a (16.0 g, 80%) as white solid. MS-ESI: [M+H]+ 201.1

Workup

  1. customA 500-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customThe solvent was removed under reduced pressure
  3. customThe resulting residue was purified by silica-gel column chromatography
  4. washeluting with 100:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-1e06132a2f1b4f2b9187287d429867c8
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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