1-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one → HCID 58014957, compound

HRID 1888943Notes

Reaction equation

HRID 1888943 reaction equation
N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:20]3)[C:14]([C:35](=[O:37])[NH2:36])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][N:48]([C:51](=[O:53])[CH3:52])[CH2:47][CH2:46]2)=[CH:41][CH:40]=1>O1CCOCC1>[C:51]([N:48]1[CH2:47][CH2:46][N:45]([C:42]2[CH:41]=[CH:40][C:39]([NH:38][C:11]3[N:16]=[C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH2:28][C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)=[O:26])[CH2:20]4)[C:14]([C:35](=[O:37])[NH2:36])=[CH:13][N:12]=3)=[CH:44][CH:43]=2)[CH2:50][CH2:49]1)(=[O:53])[CH3:52]

Participants

4

Reactant 2

HCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 58014797HCID 58014797, compound

Product 1

HCID 58014957HCID 58014957, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of benzyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)piperidine-1-carboxylate (0.404 g, 0.805 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (0.220 g, 1.00 mmol) and pTsOH monohydrate (0.167 g, 0.879 mmol) in dioxane (8 mL) was stirred at 100 C for 3 h. The mixture was then purified by HPLC to give benzyl 3-((2-(4-(4-acetylpiperazin-1-yl)phenylamino)-5-carbamoylpyrimidin-4-ylamino)methyl)piperidine-1-carboxylate 45 (0.270 g).

Workup

  1. customThe mixture was then purified by HPLC

Sources & evidence

ORD record
ord-3fa76c655d7e43a883e2484dc5ecdf0e
Source dataset
uspto-grants-2013_08
Patent number
US08501944B2

Reaction notes

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