Acetic Acid → 1,1-Diethyl-3-(6-methyl-13-methylamino-8alpha-ergolinyl)urea

HRID 35218Notes

Reaction equation

HRID 35218 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17]3[C:7]([CH2:8][C@@H:9]4[C@@H:14]([C:15]=3[CH:16]=1)[CH2:13][C@H:12]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:11][N:10]4[CH3:26])=[CH:6][NH:5]2.[C:27](O)(=O)C.CSC.B>C(O)=O>[CH2:21]([N:20]([CH2:23][CH3:24])[C:19]([NH:18][C@H:12]1[CH2:13][C@H:14]2[C@@H:9]([CH2:8][C:7]3[C:17]4[C:4](=[CH:3][C:2]([NH:1][CH3:27])=[CH:16][C:15]2=4)[NH:5][CH:6]=3)[N:10]([CH3:26])[CH2:11]1)=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 867423583-(13-Amino-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 867423571,1-Diethyl-3-(6-methyl-13-methylamino-8alpha-ergolinyl)urea

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

At -20° C., 355 mg of 3-(13-amino-6-methyl-8α-ergolinyl)-1,1-diethylurea is reacted to the N-formyl compound with the mixed anhydride of acetic acid and formic acid and the N-formyl compound is reduced with borane-dimethyl sulfide (S. Krishnamurty, Tetrahedron Letters 1982: 3315). After chromatography, 260 mg of 1,1-diethyl-3-(6-methyl-13-methylamino-8α-ergolinyl)urea is obtained.

Sources & evidence

ORD record
ord-0b54ebb2001341259c7e0f254d3e5497
Source dataset
uspto-grants-1988_08
Patent number
US04766128

Reaction notes

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