Triethylamine → HCID 86675814, compound

HRID 59877Notes

Reaction equation

HRID 59877 reaction equation
[F:1][C:2]([F:30])([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[N:19][C:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=3)=[N:17]2)=[CH:12][CH:11]=1)[C:3]([F:9])([F:8])[C:4]([F:7])([F:6])[F:5].C1(P([N:45]=[N+:46]=[N-:47])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C(O)(C)C>[F:1][C:2]([F:30])([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[N:19][C:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([N:45]=[N+:46]=[N-:47])=[O:27])=[CH:23][CH:22]=3)=[N:17]2)=[CH:12][CH:11]=1)[C:3]([F:9])([F:8])[C:4]([F:6])([F:5])[F:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 866758154-(1-(4-(Perfluoropropyl)phenyl)-1H-1,2,4-triazol-3-yl)benzoic acid

Product 1

HCID 86675814HCID 86675814, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(1-(4-(Perfluoropropyl)phenyl)-1H-1,2,4-triazol-3-yl)benzoic acid (400 mg, 0.92 mmol) was dissolved in 7 mL of isopropanol and treated with diphenylphosphoryl azide (0.300 g, 1.09 mmol) and triethylamine (0.200 g, 2.0 mmol). The solution was allowed to stir for 6 h, then it was cooled to 0° C. and the resulting solid was filtered, washed with a minimum amount of iPrOH, and dried under high vacuum to give the azide as an off-white solid (0.120 g, 30%). This solid was not further characterized, but used directly in the subsequent Curtius rearrangement to prepare molecule A113, using conditions described in Example 39.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with a minimum amount of iPrOH
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-a33441b0dd3944fda44ea0e5b23df0ef
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Reaction notes

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