Ammonia → 3-(2-Bromo-13-iodo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

HRID 35859Notes

Reaction equation

HRID 35859 reaction equation
[Br:1][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].[I:27]N1C(=O)CCC1=O.N.ClCCl>FC(F)(F)C(O)=O>[Br:1][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]=[C:13]([I:27])[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]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 130598603-(2-Bromo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 677878493-(2-Bromo-13-iodo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

42 mg of 3-(2-bromo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea (0.1 mmol) is dissolved in 2 ml of trifluoroacetic acid and mixed with 22 mg of N-iodosuccinimide (0.1 mmol). After 15 minutes of stirring at room temperature, ice is added, it is made alkaline with ammonia, and shaken out with dichloromethane. The organic phases are dried and concentrated by evaporation, the residue is chromatographed. The pure substance crystallizes from dichloromethane, yield 9 mg (16% of theory).

Workup

  1. additionice is added
  2. customThe organic phases are dried
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed
  5. customThe pure substance crystallizes from dichloromethane, yield 9 mg (16% of theory)

Sources & evidence

ORD record
ord-4a800c25941c4f0aa35f3bce26941519
Source dataset
uspto-grants-1995_05
Patent number
US05411966

Reaction notes

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