Diisopropylethylamine → HCID 22046357, compound

HRID 1830755Notes

Reaction equation

HRID 1830755 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.C(N(C(C)C)CC)(C)C.C1(P([N:37]=[N+:38]=[N-:39])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.CCOCC>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]([N:37]=[N+:38]=[N-:39])=[O:13]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 96695Quinoxaline-2-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 22046357HCID 22046357, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution quinoxaline-2-carboxylic acid (348 mg, 2 mmol) in THF (6 mL) at rt under nitrogen was treated with diisopropylethylamine (365 μL, 2.1 mmol) followed by diphenylphosphoryl azide (410 μL, 1.9 mmol). After stirring overnight the reaction was diluted to 60 mL with Et2O and washed 2×60 mL with sat. NaCl. There was an insoluble brown oil, which was drained off with the aqueous layer and assumed to be a diphenyl phosphate impurity. The organics were dried (MgSO4), filtered and concentrated to a tan solid, which corresponds to the acyl azide (350 mg, 92%). 1H-NMR (400 MHz, CDCl3) δ9.58 (s, 1H), 8.32 (d, 1H), 8.21 (d, 1H), 7.94 (m, 2H)

Workup

  1. washwashed 2×60 mL with sat. NaCl
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to a tan solid, which

Sources & evidence

ORD record
ord-47a8dcb4b9914ccf85afd2265add1361
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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