2-(4-Methylphenyl)propan-2-amine → N-[1-(4-Methylphenyl)-1-methylethyl]-3-cyanoandrosta-3,5-diene-17beta-carboxamide

HRID 962680Notes

Reaction equation

HRID 962680 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].[CH3:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([NH2:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=1>>[CH3:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([NH:41][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])([CH3:39])[CH3:40])=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 5840502-(4-Methylphenyl)propan-2-amineHCID 15380265S-2pyridyl 3-cyanoandrosta-3,5-diene-17beta-thiocarboxylate

Product 1

HCID 67646695N-[1-(4-Methylphenyl)-1-methylethyl]-3-cyanoandrosta-3,5-diene-17beta-carboxamideYield 88%

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-methylphenyl)-1-methylethylamine (prepared as described in Preparation 10h) as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained in a yield of 88%.

Sources & evidence

ORD record
ord-ca6a74caa39249d0a28300b15725a7b6
Source dataset
uspto-grants-1998_06
Patent number
US05760025

Reaction notes

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