Triethylamine → HCID 13822804, compound

HRID 1761718Notes

Reaction equation

HRID 1761718 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([C:18]#[CH:19])[NH:12]4)[CH2:5][C@H:4]([NH:20][C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:3]1.C(N(CC)CC)C.I[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1>CN(C)C=O.[Cu]I>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([C:18]#[C:19][C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)[NH:12]4)[CH2:5][C@H:4]([NH:20][C:21](=[O:27])[N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])[CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 189212-IodothiopheneHCID 13559048HCID 13559048, compound

Product 1

HCID 13822804HCID 13822804, compound

Reagents, catalysts & solvents 2

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

Procedure

Under argon, 72 mg of 3-(6-methyl-2-ethynyl-8α-ergolinyl)-1,1-diethylurea is heated in 2 ml of dimethylformamide with 2 ml of triethylamine, 1.5 mg of copper(I) iodide, 0.069 ml of 2-iodothiophene, and 4.8 mg of palladium(O) tetrakis(triphenylphosphine) for 2 hours to 80° C. After evaporation, the mixture is taken up in ethyl acetate and washed in succession with dilute ammonia solution and saturated sodium chloride solution. After chromatography over silica gel with ethyl acetate:ethanol=1:1 and recrystallization from ethanol/hexane, 26 mg of 3-[6-methyl-2-(thien-2-ylethynyl)-8α-ergolinyl]-1,1diethylurea is obtained, mp 252°-256° C.

Workup

  1. customAfter evaporation
  2. washwashed in succession with dilute ammonia solution and saturated sodium chloride solution
  3. customAfter chromatography over silica gel with ethyl acetate:ethanol=1:1 and recrystallization from ethanol/hexane

Sources & evidence

ORD record
ord-db321a0f19e04d938d667b9f1708e4e0
Source dataset
uspto-grants-1989_05
Patent number
US04826851

Reaction notes

Loading…