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

HRID 577736

Reaction equation

HRID 577736 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0961618d403b4cdb9490b64d59174ec1
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Linked notes

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