Water → HCID 86721287, compound

HRID 1750446Notes

Reaction equation

HRID 1750446 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22]C(O)=O)[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C1(P([N:40]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:43]([OH:47])(C)(C)C.[OH2:48]>C1(C)C=CC=CC=1>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][NH:40][C:43](=[O:47])[OH:48])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 867211822-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid

Product 1

HCID 86721287HCID 86721287, compoundYield 11.35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid (100 mg, 0.28 mmol), diphenylphosphoryl azide (0.066 mL, 0.31 mmol), TEA (0.047 mL, 0.33 mmol) and tert-butyl alcohol (0.052 mL, 0.56 mmol) in toluene (2.0 mL) was stirred at room temperature for 14 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 50→80% ethyl acetate/hexane) to give ((2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)methyl)carbamic acid (13.6 mg, 0.032 mmol, 11.35%) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 50→80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-900ab0b6a1644c00a8b9a7cffffed699
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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