S-2pyridyl 3-cyanoandrosta-3,5-diene-17beta-thiocarboxylate → N-[1-(4-Ethoxyphenyl)-1-methylethyl]-3-cyanoandrosta-3,5-diene-17beta-carboxamide

HRID 1735535Notes

Reaction equation

HRID 1735535 reaction equation
[C:1]([C:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:22](=[O:30])SC2C=CC=CN=2)[CH:4]=1)#[N:2].[CH2:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([NH2:43])([CH3:42])[CH3:41])=[CH:36][CH:35]=1)[CH3:32]>>[CH2:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([NH:43][C:22]([C@H:12]2[CH2:11][CH2:10][C@H:9]3[C@H:8]4[C@H:17]([CH2:16][CH2:15][C@:13]23[CH3:14])[C@:18]2([CH3:21])[C:5]([CH:4]=[C:3]([C:1]#[N:2])[CH2:20][CH2:19]2)=[CH:6][CH2:7]4)=[O:30])([CH3:42])[CH3:41])=[CH:36][CH:35]=1)[CH3:32]

Participants

3

Reactant 2

HCID 15380265S-2pyridyl 3-cyanoandrosta-3,5-diene-17beta-thiocarboxylateHCID 230091172-(4-Ethoxyphenyl)propan-2-amine

Product 1

HCID 67645575N-[1-(4-Ethoxyphenyl)-1-methylethyl]-3-cyanoandrosta-3,5-diene-17beta-carboxamideYield 91%

Procedure

Following a procedure similar to that described in Example 3(b), but using S-2-pyridyl 3-cyanoandrosta-3,5-diene-17β-thiocarboxylate [prepared as described in Example 3(a)] and 1-(4-ethoxyphenyl)-1-methylethylamine (prepared as described in Preparation 10g) as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained in a yield of 91%.

Sources & evidence

ORD record
ord-eaf15958846942b584357f4c5a30468c
Source dataset
uspto-grants-1996_07
Patent number
US05536714

Reaction notes

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