Triethylamine → HCID 11201236, compound

HRID 966151Notes

Reaction equation

HRID 966151 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([NH:11][O:12][CH3:13])=[O:10])=[CH:4][C:3]=1[NH:14][C:15]1[C:20]2=[C:21]([CH:27]([CH3:29])[CH3:28])[C:22]([C:24]([OH:26])=O)=[CH:23][N:19]2[N:18]=[CH:17][N:16]=1.C(N(CC)CC)C.C1(P([N:51]=[N+:52]=[N-:53])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9](=[O:10])[NH:11][O:12][CH3:13])=[CH:4][C:3]=1[NH:14][C:15]1[C:20]2=[C:21]([CH:27]([CH3:28])[CH3:29])[C:22]([C:24]([N:51]=[N+:52]=[N-:53])=[O:26])=[CH:23][N:19]2[N:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11407063HCID 11407063, compound

Product 1

HCID 11201236HCID 11201236, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of Example 22 (1.11 g, 2.74 mmol) in dioxane (25 mL) was added triethylamine (0.57 mL, 4.1 mmol) followed by diphenylphosphoryl azide (0.77 mL, 3.57 mmol) and the resulting mixture was stirred at 40° C. After 1 h, the mixture was concentrated and the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexanes to afford acyl azide, 4-(2,4-difluoro-5-methoxycarbamoyl-phenylamino)-5-isopropyl-pyrrolo[2, 1-f][1,2,4]triazine-6-carbonyl azide (0.95 g, 81%) as pale yellow foam.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ca6ae11b96cf406daa6bea2a70440a6f
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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