Diisopropylamine → HCID 86743467, compound

HRID 2352075Notes

Reaction equation

[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][C:13]=3[C:23]#[CH:24])[N:9]([CH3:25])[CH2:8]1)=[O:5])[CH3:2].[CH:28]([N-]C(C)C)([CH3:30])[CH3:29].[Li+].C(NC(C)C)(C)C.C([Li])CCC.C(I)CC>O1CCCC1>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[N:14]([CH2:29][CH2:28][CH3:30])[C:13]=3[C:23]#[CH:24])[N:9]([CH3:25])[CH2:8]1)=[O:5])[CH3:27]

Participants

Conditions

Temperature: -20 °C

Procedure

Under argon, 109 mg of 1,1-diethyl-3-(2-ethynyl-6-methyl-8α-ergolinyl)urea in 5 ml of absolute tetrahydrofuran is added dropwise at -30° C. to a solution of lithium diisopropylamide, prepared from 0.15 ml of diisopropylamine and 1.8 ml of 0.6-molar n-butyllithium solution (hexane) in 3 ml of absolute tetrahydrofuran at 0° C. within 15 minutes. After 30 minutes of agitation at -30° C., 0.07 ml of propyl iodide is added thereto. The mixture is stirred for one hour at -20° C. and overnight at room temperature. After evaporation, the mixture, after adding sodium bicarbonate solution and a small amount of ethanol, is extracted by shaking with ethyl acetate. The organic phase is concentrated and chromatographed over silica gel with toluene:glacial acetic acid:water=10:10:1, thus obtaining 30 mg of 1,1-diethyl-3-(2-ethynyl-1-propyl-6-methyl-8α-ergolinyl)urea as an oil.

Workup

customAfter evaporation
additionthe mixture, after adding sodium bicarbonate solution
extractiona small amount of ethanol, is extracted
stirringby shaking with ethyl acetate
concentrationThe organic phase is concentrated
customchromatographed over silica gel with toluene

Sources & evidence

ORD record: ord-a7f4814ef90c4b43bdb9aa243495f134
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04874768

Reaction notes

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