Ammonia → Terguride

HRID 231703Notes

Reaction equation

HRID 231703 reaction equation
C(OC([C:11]1[NH:25][C:24]2[C:26]3[C:12]=1[CH2:13][C@@H:14]1[C@@H:19]([C:20]=3[CH:21]=[CH:22][CH:23]=2)[CH2:18][C@H:17]([NH:27][C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])[CH2:16][N:15]1[CH3:35])=O)C1C=CC=CC=1.N>C(O)CO>[CH2:33]([N:30]([CH2:31][CH3:32])[C:28](=[O:29])[NH:27][C@H:17]1[CH2:18][C@H:19]2[C@@H:14]([CH2:13][C:12]3[C:26]4[C:24](=[CH:23][CH:22]=[CH:21][C:20]2=4)[NH:25][CH:11]=3)[N:15]([CH3:35])[CH2:16]1)[CH3:34]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 135590328alpha-(3,3-Diethylureido)-6-methylergoline-2-carboxylic acid benzyl ester

Product 1

HCID 443951TergurideYield 85.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

150 mg (0.31 mmol) of 8α-(3,3-diethylureido)-6-methylergoline-2-carboxylic acid benzyl ester is heated in 3 ml of a saturated solution of ammonia in ethylene glycol for 3 hours to 100° C. After dilution with water, the mixture is extracted with ethyl acetate and the organic phase washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The residue is chromatographed over silica gel with methylene chloride/ethanol=8:1. After trituration in ethanol/hexane/ether, 90 mg of 8α-(3,3-diethylureido)-6-methylergoline)-2-carboxylic acid amide is obtained, mp 171°-173° C.

Workup

  1. extractionAfter dilution with water, the mixture is extracted with ethyl acetate
  2. washthe organic phase washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel with methylene chloride/ethanol=8:1

Sources & evidence

ORD record
ord-5ae42176cf7842f7b288a3e270eab8ce
Source dataset
uspto-grants-1989_07
Patent number
US04847262

Reaction notes

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