Toluene → tert-Butyl N-{4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridyl}carbamate

HRID 1828428Notes

Reaction equation

HRID 1828428 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13](C(O)=O)[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].C1(C)C=CC=CC=1.C([N:29]([CH2:32]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:41])C=CC=CC=1.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:29][C:32](=[O:41])[O:55][C:51]([CH3:54])([CH3:53])[CH3:52])[CH:12]=2)[S:7][CH:8]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 1140TolueneHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 220636014-[(4-Isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinecarboxylic acid

Product 1

HCID 22063558tert-Butyl N-{4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridyl}carbamateYield 53%

Conditions

Temperature
140 °C

Procedure

4-[(4-Isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinecarboxylic acid (50 mg, 0.18 mmol) was added with toluene (12 ml), triethylamine (63 pl, 0.45 mmol) and diphenyl phosphorylazide (78 μl, 0.36 mmol) and refluxed by heating at 140° C. for 7 hours. The reaction solution was returned to room temperature, added with tert-butanol (12 ml) and refluxed again by heating at 140° C. The reaction solution was stirred for 18 hours and then returned to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1) to obtain 33 mg (53%) of the title compound.

Workup

  1. temperaturerefluxed
  2. customwas returned to room temperature
  3. temperaturerefluxed again
  4. temperatureby heating at 140° C
  5. customreturned to room temperature
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-99c891d49e4e43e4ae50cdbd6c776113
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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