Triethylamine → 3-[2-(4-Cyanophenylethynyl)-6-methyl-8alpha-ergolinyl]-1,1-diethylurea

HRID 1761719Notes

Reaction equation

HRID 1761719 reaction equation
I[C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:7][N:6]1[CH3:26].C(N(CC)CC)C.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:42]#[CH:43])=[CH:38][CH:37]=1)#[N:35]>CN(C=O)C.[Cu]I>[C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:42]#[C:43][C:2]2[NH:16][C:15]3[C:17]4[C:3]=2[CH2:4][C@@H:5]2[C@@H:10]([C:11]=4[CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:8]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:7][N:6]2[CH3:26])=[CH:38][CH:37]=1)#[N:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 45472454-EthynylbenzonitrileHCID 135590301,1-Diethyl-3-(2-iodo-6-methyl-8alpha-ergolinyl)urea

Product 1

HCID 138228103-[2-(4-Cyanophenylethynyl)-6-methyl-8alpha-ergolinyl]-1,1-diethylureaYield 43.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

Under argon, 200 mg of 3-(2-iodo-6-methyl-8α-ergolinyl)-1,1-diethylurea is heated to 80°-90° C. in 4 ml of DMF with 4 ml of triethylamine, 4 mg of copper(I) iodide, 8 mg of palladium(O) tetrakis(triphenylphosphine) and 112 mg of 4-cyanophenylacetylene for 2 hours. After evaporation, the mixture is distributed in ethyl acetate and saturated sodium bicarbonate solution, and the organic phase is washed with saturated sodium chloride solution. After chromatography over silica gel with methylene chloride:ethanol=10:1, 87 mg of 3-[2-(4-cyanophenylethynyl)-6-methyl-8α-ergolinyl]-1,1-diethylurea is obtained, mp 150°-151° C., [α]D =+139.5° (c=0.2; pyridine).

Workup

  1. customAfter evaporation
  2. washsaturated sodium bicarbonate solution, and the organic phase is washed with saturated sodium chloride solution

Sources & evidence

ORD record
ord-4602344eb51a40ec90c56811d3de7ba5
Source dataset
uspto-grants-1989_05
Patent number
US04826851

Reaction notes

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