1-(2-Pyridyl)piperazine → HCID 15981038, compound

HRID 1957932Notes

Reaction equation

HRID 1957932 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])[CH: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[C:3]([C:22]([N:56]2[CH2:57][CH2:58][N:53]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][N:47]=3)[CH2:54][CH2:55]2)=[O:23])=[CH:4][C:5]([NH:7][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]([F:20])([F:21])[F:19])=[CH:15][CH:16]=2)=[O:9])=[CH:6]1

Participants

6

Reactant 3

HCID 944591-(2-Pyridyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59363504HCID 59363504, compound

Product 1

HCID 15981038HCID 15981038, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

50 mg (0.15 mmol) of 1-methyl-4[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-pyrrole-2-carboxylic acid (Example 5A) are initially charged in 1 ml of DMF, and 56 mg (0.18 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) and 8.9 mg (0.07 mmol) of 4-(dimethylamino)pyridine (DMAP) are added. 29 mg (0.18 mmol) of 1-(2-pyridyl)piperazine are then added, and the mixture is stirred at RT for 8 h. The reaction solution is purified by RP-HPLC (acetonitrile/water). This gives a solid.

Workup

  1. customThe reaction solution is purified by RP-HPLC (acetonitrile/water)
  2. customThis gives a solid

Sources & evidence

ORD record
ord-8e2de5afb87642b8bc5effe46660d0c9
Source dataset
uspto-grants-2013_04
Patent number
US08410090B2

Reaction notes

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