Tert-butyl 4-(4-{[4-carbamoyl-2-(naphthalen-2-ylamino)thiazol-5-yl]carbamoyl}benzyl)piperazine-1-carboxylate → 2-(Naphthalen-2-ylamino)-5-[4-(piperazin-1-ylmethyl)benzamido]thiazole-4-carboxamide

HRID 512534Notes

Reaction equation

HRID 512534 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([NH:32][C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=2)[S:7][C:8]=1[NH:9][C:10]([C:12]1[CH:31]=[CH:30][C:15]([CH2:16][N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[CH:14][CH:13]=1)=[O:11])(=[O:3])[NH2:2]>Cl.O1CCOCC1>[CH:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:41]=[CH:42][C:33]=1[NH:32][C:6]1[S:7][C:8]([NH:9][C:10](=[O:11])[C:12]2[CH:13]=[CH:14][C:15]([CH2:16][N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[CH:30][CH:31]=2)=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=1

Participants

3

Reactant 1

HCID 86703373Tert-butyl 4-(4-{[4-carbamoyl-2-(naphthalen-2-ylamino)thiazol-5-yl]carbamoyl}benzyl)piperazine-1-carboxylate

Product 1

HCID 725504112-(Naphthalen-2-ylamino)-5-[4-(piperazin-1-ylmethyl)benzamido]thiazole-4-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of tert-butyl 4-(4-{[4-carbamoyl-2-(naphthalen-2-ylamino)thiazol-5-yl]carbamoyl}benzy)piperazine-1-carboxylate (0.025 g, 0.04 mmol) in 4N HCl-dioxane (5 mL) was stirred for 2 hrs at rt under N2-atmosphere. The solvent was evaporated in vacuo, and the residue was washed with ether and purified by silica gel column chromatography eluted with 50% EtOAc in hexane to give 0.013 g (68% yield) of the titled compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washthe residue was washed with ether
  3. custompurified by silica gel column chromatography
  4. washeluted with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-1a2d64487fe941ca89ec9f6737a140d6
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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