Diisopropylethylamine → HCID 13770879, compound

HRID 1249598Notes

Reaction equation

HRID 1249598 reaction equation
[N:1]([CH2:4][C:5]1[NH:6][CH:7]=[C:8]([O:12]CC2C=CC=CC=2)[C:9](=[O:11])[CH:10]=1)=[N+]=[N-].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H].C(N(C(C)C)CC)(C)C>CN(C)C=O.[Pd]>[NH2:1][CH2:4][C:5]1[NH:6][CH:7]=[C:8]([OH:12])[C:9](=[O:11])[CH:10]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 13770878HCID 13770878, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13770879HCID 13770879, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-(azidomethyl)-5-[(phenylmethyloxy)]-4-oxo-1,4-dihydropyridine (641 mg, 2.5 mmole) in 7 ml of dimethylformamide was treated with p-toluenesulfonic acid monohydrate (951 mg, 5 mmole), and the resulting solution was treated with 10% palladium on charcoal (641 mg). The mixture was stirred under 1 atmosphere of hydrogen for 75 minutes. The hydrogen was purged with argon, and diisopropylethylamine (871 μl, 5 mmole) was added. The resulting mixture was used immediately in the following reaction.

Workup

  1. additionwas added
  2. customThe resulting mixture was used immediately in the following reaction

Sources & evidence

ORD record
ord-6c09aaef0e6746e695886013a95059ef
Source dataset
uspto-grants-1986_12
Patent number
US04632985

Reaction notes

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