Acetylene → Tert-butyl 4-[4-({4-[2-(tert-butoxycarbonyl)hydrazino]carbonylmethylphenyl}ethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 1465439Notes

Reaction equation

HRID 1465439 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1)#[CH:2].Br[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:30])=[CH:24][CH:23]=1.C#C>>[C:36]([O:35][C:33]([NH:32][NH:31][C:29]([CH2:28][C:25]1[CH:24]=[CH:23][C:22]([C:2]#[C:1][C:3]2[N:4]=[C:5]([CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[S:6][CH:7]=2)=[CH:27][CH:26]=1)=[O:30])=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

4

Reactant 3

HCID 6326AcetyleneHCID 58181284Tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylateHCID 67029623Tert-butyl 2-[(4-bromophenyl)acetyl]hydrazinecarboxylate

Product 1

HCID 58181310Tert-butyl 4-[4-({4-[2-(tert-butoxycarbonyl)hydrazino]carbonylmethylphenyl}ethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylateYield 18%

Procedure

Using tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate and tert-butyl 2-[(4-bromophenyl)acetyl]hydrazinecarboxylate as starting materials, Sonogashira-Castero-Stephens acetylene coupling was performed under reaction conditions similar to those of Production Example 1, step 4 to give tert-butyl 4-[4-({4-[2-(tert-butoxycarbonyl)hydrazino]carbonylmethylphenyl}ethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (yield 18%).

Workup

  1. customwas performed under reaction conditions similar to those of Production Example 1, step 4

Sources & evidence

ORD record
ord-d321eac32acc44e9a19a67bc8a6dfba8
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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