Dimethylformamide → HCID 10089126, compound

HRID 986533Notes

Reaction equation

HRID 986533 reaction equation
[H-].[Na+].[CH:3]([C:6]1[NH:7][CH:8]=[CH:9][N:10]=1)([CH3:5])[CH3:4].CN(C)C=O.S(C1C=CC(C)=CC=1)(O[CH2:20][C@@H:21]1[CH2:35][C@H:34]2[C@@H:24]([CH2:25][C:26]3[C:36]4[C:29](=[CH:30][CH:31]=[CH:32][C:33]2=4)[NH:28][CH:27]=3)[N:23]([CH3:37])[CH2:22]1)(=O)=O>CO.C(O)(C)C>[CH:3]([C:6]1[N:7]([CH2:20][C@@H:21]2[CH2:35][C@H:34]3[C@@H:24]([CH2:25][C:26]4[C:36]5[C:29](=[CH:30][CH:31]=[CH:32][C:33]3=5)[NH:28][CH:27]=4)[N:23]([CH3:37])[CH2:22]2)[CH:8]=[CH:9][N:10]=1)([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 10089126HCID 10089126, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

0.9 g of 50% sodium hydride in an oil was added to a mixture of 4.0 g of 2-isopropylimidazole and 40 ml of dimethylformamide, and the mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 2 hours. The solvent was distilled off under reduced pressure, and water was added to the residue. The precipitated crystals were filtered, washed with water and purified by silica gel column chromatography (eluted with acetone). The crystals thus obtained were dissolved in methanol, and isopropyl alcohol was added thereto. The mixture was concentrated and allowed to cool to obtain 0.6 g of the titled compound as colorless needles having a melting point of 283°-288° C. (with decomposition).

Workup

  1. temperaturewas then heated on a water bath for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. filtrationThe precipitated crystals were filtered
  5. washwashed with water
  6. custompurified by silica gel column chromatography (eluted with acetone)
  7. customThe crystals thus obtained
  8. concentrationThe mixture was concentrated
  9. temperatureto cool

Sources & evidence

ORD record
ord-9a9013f5ba1f42f890f7f835d7a36766
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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