1-(2-Pyridyl)piperazine → N-{1-Methyl-2-[(4-pyridin-2-yl-piperazin-1-yl)carbonyl]-1H-imidazol-4-yl}-N'-[4-(trifluoromethoxy)phenyl]urea

HRID 2277419Notes

Reaction equation

HRID 2277419 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[N:4]=[C:3]1[C:22](O)=[O:23].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[N:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:20])([F:19])[F:21])=[CH:13][CH:12]=2)=[O:9])[N:4]=[C:3]1[C:22]([N:56]1[CH2:57][CH2:58][N:53]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][N:47]=2)[CH2:54][CH2:55]1)=[O:23]

Participants

6

Reactant 3

HCID 944591-(2-Pyridyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 594218021-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic Acid

Product 1

HCID 11858022N-{1-Methyl-2-[(4-pyridin-2-yl-piperazin-1-yl)carbonyl]-1H-imidazol-4-yl}-N'-[4-(trifluoromethoxy)phenyl]urea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

1.50 g (4.36 mmol) of the compound of Example 4A is dissolved in 30 ml of DMF and mixed with 1.82 g (5.66 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) and 266 mg (2.18 mmol) of 4-dimethylaminopyridine. After adding 925 mg (5.66 mmol) of 1-(pyridin-2-yl)-piperazine, it is allowed to stir for 4 hours at room temperature. The reaction mixture is purified by RP-HPLC.

Workup

  1. customThe reaction mixture is purified by RP-HPLC

Sources & evidence

ORD record
ord-8aa9c0bcccca4aea9e08358dbb41e03c
Source dataset
uspto-grants-2015_09
Patent number
US09133165B2

Reaction notes

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