Triethylamine → HCID 13979034, compound

HRID 2407760Notes

Reaction equation

HRID 2407760 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]([C:12]([O:14][CH3:15])=[O:13])=[CH:3]1.C1(P([N:30]=[N+:31]=[N-:32])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[N:30]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1)=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 821167Methyl 4-Hydroxyquinoline-2-carboxylate

Product 1

HCID 13979034HCID 13979034, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the compound prepared in Example 272 (0.032 g) in N,N-dimethylformamide (1 mL) was treated with diphenyl phosphoryl azide (0.037 mL), followed by triethylamine (0.028 mL) at room temperature. The mixture was heated at 100° C. overnight. The solvent was evaporated in vacuo and the resulting oil was purified by column chromatography on silica gel (1-10% diethyl ether in dichloromethane) to obtain the title compound (0.016 g) having the following physical data.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe resulting oil was purified by column chromatography on silica gel (1-10% diethyl ether in dichloromethane)

Sources & evidence

ORD record
ord-2baec9f651174a1aafc7e445fd810bb6
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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