Benzyl Alcohol → benzyl (3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazol-5-yl)carbamate

HRID 577736

Reaktionsgleichung

Reaktionsgleichung von HRID 577736
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9](C(O)=O)[N:8]([CH3:14])[N:7]=1.C([N:18]([CH2:21]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1(C)C=CC=CC=1>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([NH:18][C:21](=[O:30])[O:47][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:8]([CH3:14])[N:7]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 866796683-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylic acid

Produkt 1

HCID 86679669benzyl (3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazol-5-yl)carbamateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylic acid (3.3 g, 15.5 mmol) and triethylamine (2.35 g, 23.2 mmol) in dry toluene (50 mL) was added DPPA (4.69 g, 17 mmol) under N2 and the mixture was refluxed for 1 hr. After the addition of benzyl alcohol (3.35 g, 31 mmol), the mixture was refluxed overnight. The mixture was concentrated in vacuo to give crude product, which was purified by column chromatography (silica gel, CH2Cl2/MeOH 30:1) to give the title compound (1.42 g, 29% yield) as a colorless oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hr
  2. temperaturethe mixture was refluxed overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. customto give crude product, which
  5. customwas purified by column chromatography (silica gel, CH2Cl2/MeOH 30:1)

Quellen und Nachweise

ORD-Eintrag
ord-0961618d403b4cdb9490b64d59174ec1
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040547B2

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