Ammonia → HCID 67814194, compound

HRID 35856Notes

Reaction equation

HRID 35856 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[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][C:17]([C:23](O)([CH3:25])[CH3:24])=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:27])[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.N>O1CCCC1.C(OCC)(=O)C>[CH2:29]([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][C:17]([C:23]([CH3:25])=[CH2:24])=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:27])[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:30]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67788699HCID 67788699, compound

Product 1

HCID 67814194HCID 67814194, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

208 mg of 1,1-diethyl-3-[13-(1-hydroxy-1-methyl-ethyl)-2,6- -dimethyl-8alpha-ergolinyl]-urea (0.5 mmol) is dissolved in 20 ml of anhydrous tetrahydrofuran, mixed with 0.7 ml of triethylamine (5 mmol) and 0.4 ml of methanesulfonic acid chloride (5 mmol) and stirred for 30 minutes at room temperature. Ice is added to the mixture, it is made alkaline with conc. ammonia and shaken out with ethyl acetate. The residue is chromatographed on silica gel with dichloromethane/methanol, yield 99 mg (50% of theory).

Workup

  1. additionIce is added to the mixture, it
  2. customThe residue is chromatographed on silica gel with dichloromethane/methanol, yield 99 mg (50% of theory)

Sources & evidence

ORD record
ord-7e347f381399444c85e95d1bcfd2d912
Source dataset
uspto-grants-1995_05
Patent number
US05411966

Reaction notes

Loading…