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

HRID 1828428
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HRID 1828428 반응식
[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]
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참가 물질

6

반응물 5

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

생성물 1

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

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온도
140 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-99c891d49e4e43e4ae50cdbd6c776113
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07056917B2

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