Pyrazole → 1-(6-Methylergolin-8beta-ylmethyl)pyrazole

HRID 986526Notes

Reaction equation

HRID 986526 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.S(C1C=CC(C)=CC=1)(O[CH2:12][C@@H:13]1[CH2:27][C@H:26]2[C@@H:16]([CH2:17][C:18]3[C:28]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]2=4)[NH:20][CH:19]=3)[N:15]([CH3:29])[CH2:14]1)(=O)=O>CN(C)C=O>[CH3:29][N:15]1[C@H:16]2[C@@H:26]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:28]=3[C:18]([CH2:17]2)=[CH:19][NH:20]4)[CH2:27][C@@H:13]([CH2:12][N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)[CH2:14]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 100637651-(6-Methylergolin-8beta-ylmethyl)pyrazoleYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.7 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.5 g of pyrazole and 20 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.5 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 1 hour. The solvent was distilled off under reduced pressure, and water was added to the residue. The precipitated crystals were separated by filtration, washed with water and recrystallized from dichloromethane-isopropyl ether to obtain 1.7 g of the titled compound as colorless flakes having a melting point of 192°-194° C.

Workup

  1. temperaturewas then heated on a water bath for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. customThe precipitated crystals were separated by filtration
  5. washwashed with water
  6. customrecrystallized from dichloromethane-isopropyl ether

Sources & evidence

ORD record
ord-67ff8f4531cc4717ad8d4e56c8a8ed56
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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