1-Methylpiperazine → {3-[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino}-phenyl}-(4-methyl-piperazin-1-yl)methanone

HRID 1012179Notes

Reaction equation

HRID 1012179 reaction equation
[Br:1][C:2]1[S:6][C:5](NC2C=CC(C(O)=O)=CC=2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([O-:23])=O.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CCN(C(C)C)C(C)C.CN(C(O[N:51]1N=NC2[CH:54]=[CH:55][CH:56]=[N:57][C:52]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O.CS(C)=O>[Br:1][C:2]1[S:6][C:5]([C:56]2[CH:55]=[CH:54][N:51]=[C:52]([NH:17][C:18]3[CH:19]=[C:20]([C:21]([N:31]4[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]4)=[O:23])[CH:24]=[CH:25][CH:26]=3)[N:57]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 30141453-AminobenzoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866126254-(5-Bromo-thiophen-2-ylamino]-benzoic acid

Product 1

HCID 16666647{3-[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino}-phenyl}-(4-methyl-piperazin-1-yl)methanoneYield 79.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 31374DimethylacetamideSolvent

Procedure

3-[4-(5-Bromo-thiophen-2-ylamino]-benzoic acid (20 mg, 0.048 mmol), prepared using method 2 (step 3) and 3-aminobenzoate, was combined with N-methylpiperazine (8.1 uL, 0.073 mmol), DIEA (29.2 uL, 0.168 mmol) and HATU (27.7 mg, 0.073 mmol) in a Smith microwave vial (0.2-5.0 mL) in 0.5 mL DMA. The mixture was micro waved at 90° C. for 900 s. The solution was diluted with 0.5 mL DMSO and purified by preparative HPLC to afford {3-[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino}-phenyl}-(4-methyl-piperazin-1-yl)methanone (17.8 mg, 79.1%) after lyophilization. MS: m/z 458 (M+H+).

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-de61d50d355b48a18618f6a83f118801
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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