2-Methylpiperazine → 4-(3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

HRID 1876646Notes

Reaction equation

HRID 1876646 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:17][CH:18]1[CH2:23][NH:22][CH2:21][CH2:20][NH:19]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.O(C(C)(C)C)[Na]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:17][CH:18]1[NH:19][CH2:20][CH2:21][N:22]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH2:23]1

Participants

7

Reactant 4

HCID 660572-MethylpiperazineHCID 6693044-bromo-N-(1,3-thiazol-2-yl)benzene-1-sulfonamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 594661204-(3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamideYield 77.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Synthesized according to general procedure 8. The reaction was set up with 4-bromo-N-(thiazol-2-yl)benzenesulfonamide (1.0 g, 3.1 mmol), 2-methylpiperazine (310 mg, 3.1 mmol), Pd2(dba)3 (56 mg, 0.061 mmol), 2-(di-t-butylphosphino)biphenyl (73 mg, 0.25 mmol), NaO-tBu (930 mg, 0.25 mmol), and toluene (7.0 mL) to obtain the desired amine as a tan solid (800 mg, 2.4 mmol, 76% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=339.3; tR=0.68 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-0d3d625235af4610938bb4539e97dd69
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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