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

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]

Participants

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

temperatureto cool
temperatureunder cooling
extractionThe mixture is extracted
customthe organic phase is dried
customevaporated

Sources & evidence

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

Linked notes

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