2-Methylpiperazine, (R)- → (R)-4-(3-methylpiperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 1876649Notes

Reaction equation

HRID 1876649 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:18][C@@H:19]1[CH2:24][NH:23][CH2:22][CH2:21][NH:20]1.O(C(C)(C)C)[Na]>C1(C)C=CC=CC=1>[CH3:18][C@H:19]1[NH:20][CH2:21][CH2:22][N:23]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][N:13]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH2:24]1

Participants

5

Reactant 3

HCID 73304342-Methylpiperazine, (R)-HCID 594657044-bromo-N-(pyrimidin-4-yl)benzenesulfonamideHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 59465692(R)-4-(3-methylpiperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Synthesized according to general procedure 8. The reaction was set up with 4-bromo-N-(pyrimidin-4-yl)benzenesulfonamide (2.4 mmol), (R)-2-methylpiperazine (4.7 mmol), Pd(dba)3 (0.12 mmol) 2-(di-t-butylphosphino)biphenyl (0.50 mmol), NaO-tBu (10 mmol), and toluene (12 mL). For the purification, 10% MeOH in CH2Cl2 with the addition of 1% triethylamine was used as a solvent system to obtain the desired amine as a white solid. (900 mg, 100% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=334.3; tR=0.4 min.

Workup

  1. customSynthesized
  2. customFor the purification, 10% MeOH in CH2Cl2
  3. additionwith the addition of 1% triethylamine

Sources & evidence

ORD record
ord-d1c95e0b58a44e5a9de9db6aa6f9eb5f
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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