tert-Butanol → HCID 67299946, compound

HRID 1260328Notes

Reaction equation

HRID 1260328 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:5][C:4](C(O)=O)=[N:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])C=CC=CC=1.C([N:35]([CH2:38]C)CC)C.[C:40]([OH:44])([CH3:43])([CH3:42])[CH3:41]>>[C:40]([O:44][C:38](=[O:23])[NH:35][C:4]1[CH:5]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:2]([CH3:1])[N:3]=1)([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azide2×HCID 22494359HCID 22494359, compound

Product 1

HCID 67299946HCID 67299946, compound

Conditions

Temperature
90 °C

Procedure

A solution of 1-methyl-5-pyridin-2-yl-1H-pyrazole-3-carboxylic acid (205 mg, 1.0 mmol) in tert-butanol (3.8 ml) was treated with diphenylphosphoryl azide (225 μl, 1.0 mmol) and triethylamine (280 μl, 2.0 mmol) and stirred at 90° C. for 24 hours. Since the reaction was not completed, another equivalent of diphenylphosphoryl azide (225 μl) and two equivalents of triethylamine (280 μl) were added and stirring was continued at 90° C. for another 24 hours. The crude product was purified by silica gel chromatography using a heptane/ethyl acetate gradient and the final product was obtained as off-white solid (66 mg, 24%).

Workup

  1. stirringstirring
  2. waitwas continued at 90° C. for another 24 hours
  3. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-751ce16127794c0b8c614ad977412caf
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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