tert-Butanol → HCID 67299900, compound

HRID 1260332Notes

Reaction equation

HRID 1260332 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:11]=[C:10](C(O)=O)[CH:9]=[N:8]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.C([N:34]([CH2:37]C)CC)C.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:37](=[O:22])[NH:34][C:10]1[CH:9]=[N:8][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:11]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 80271701-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLIC ACID

Product 1

HCID 67299900HCID 67299900, compoundYield 69%

Conditions

Temperature
90 °C

Procedure

A solution of 1-pyridin-2-yl-1H-pyrazol-4-carboxylic acid (200 mg, 1.06 mmol) in tert-butanol (4.0 ml) was treated with diphenylphosphoryl azide (240 μl, 1.06 mmol) and triethylamine (300 μl, 2.12 mmol) and stirred at 90° C. for 3 hours. The solvent was removed and the crude product was purified by silica gel chromatography using a heptane/ethyl acetate gradient to yield the product as light yellow solid (190 mg, 69%). MS: M=261.1 (M+H)+

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3f2909fbf43d442f8c19cbcda130ca77
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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