Trifluoroacetic acid → HCID 14107799, compound

HRID 2291828Notes

Reaction equation

HRID 2291828 reaction equation
C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.[CH3:15][N:16]1[C@H:30]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:31]=3[C:28]([CH2:29]2)=[CH:27][NH:26]4)=[CH:19][C@@H:18]([CH2:32][S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:17]1>>[CH3:15][N:16]1[C@H:30]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:31]=3[C:28]([CH2:29]2)=[CH:27][NH:26]4)=[CH:19][C@@H:18]([CH2:32][S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:17]1.[CH3:15][N:16]1[C@H:30]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:31]=3[C@H:28]([CH2:29]2)[CH2:27][NH:26]4)=[CH:19][C@@H:18]([CH2:32][S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 98846589,10-Didehydro-6-methyl-8 beta-(2-pyridylthiomethyl)ergoline

Product 2

HCID 98846589,10-Didehydro-6-methyl-8 beta-(2-pyridylthiomethyl)ergolineHCID 14107799HCID 14107799, compoundYield 76%

Procedure

(5β,8β)-9,10-didehydro-6-methyl-8-(2-pyridylthiomethyl)ergoline was prepared as described by Stutz et al., J. Med. Chem 1978, 21, 754. Following procedures essentially as described in Example 1, a mixture of 12 ml of TFA, 2.9 g (25.0 mmol) of triethylsilane and 2.23 g (6.4 mmol) (5β,8β)-9,10-didehydro-6-methyl-8-(2pyridylthiomethyl)ergoline was stirred overnight and gave 0.85 g of the title compound (38%) following HPLC (5% methanol/chloroform/0.5% ammonium hydroxide) and recrystallization from diethyl ether/hexane, mp. 68°-71° C.

Sources & evidence

ORD record
ord-5ed71f7672ef4c83872ea0bc52101d62
Source dataset
uspto-grants-1989_01
Patent number
US04798834

Reaction notes

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