Triethylamine → HCID 178502677, compound

HRID 407781Notes

Reaction equation

HRID 407781 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 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 150a (16.0 g, 80%) as a 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-6be12b2ea2ab4ed9ac0d00021bd12737
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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