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Ammonia → 3-(9,10-Didehydro-12-ethylamino-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

HRID 35217
Notes
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Reaction equation

HRID 35217 reaction equation
[C:1]([NH:4][C:5]1[C:19]2=[C:20]3[C:8]([NH:9][CH:10]=[C:11]3[CH2:12][C@@H:13]3[C:18]2=[CH:17][C@H:16]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:15][N:14]3[CH3:29])=[CH:7][CH:6]=1)(=O)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.Cl.N.C(O)(=O)C(C(C(O)=O)O)O>O1CCOCC1.C1(C)C=CC=CC=1.O>[CH2:1]([NH:4][C:5]1[C:19]2=[C:20]3[C:8]([NH:9][CH:10]=[C:11]3[CH2:12][C@@H:13]3[C:18]2=[CH:17][C@H:16]([NH:21][C:22](=[O:28])[N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])[CH2:15][N:14]3[CH3:29])=[CH:7][CH:6]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8752,3-Dihydroxybutanedioic AcidHCID 21225700DiisobutylaluminumhydrideHCID 867423563-(12-Acetylamino-9,10-didehydro-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 86742355
3-(9,10-Didehydro-12-ethylamino-6-methyl-8alpha-ergolinyl)-1,1-diethylurea
Yield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

200 mg of 3-(12-acetylamino-9,10-didehydro-6-methyl-8α-ergolinyl)-1,1-diethylurea is dissolved in 10 ml of dioxane, combined with 2 ml of 20% diisobutyl aluminum hydride solution in toluene, and heated to 100° C. for 7 hours. The mixture is allowed to cool, then, under cooling, first water, thereafter 2N hydrochloric acid are added thereto, and the solution is rendered alkaline with dilute ammonia, after adding about 1 g of tartaric acid. The mixture is extracted by shaking with methylene chloride, the organic phase is dried and evaporated. The residue is charomatographed as disclosed in Example 7, thus producing 135 mg of 3-(9,10-didehydro-12-ethylamino-6-methyl-8α-ergolinyl)-1,1-diethylurea.

Workup

  1. temperatureto cool
  2. temperatureunder cooling
  3. extractionThe mixture is extracted
  4. customthe organic phase is dried
  5. customevaporated

Sources & evidence

ORD record
ord-5ab883efae4c44dbb6f8600b043a3b98
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766128

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes