p-Toluenesulfonic acid → HCID 58015888, compound

HRID 2189344Notes

Reaction equation

HRID 2189344 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:4][N:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][N:37]([C:40](=[O:42])[CH3:41])[CH2:36][CH2:35]2)=[CH:30][CH:29]=1>CN(C=O)C.CCOC(C)=O>[CH2:12]([CH:11]([N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH:27][C:28]1[CH:29]=[CH:30][C:31]([N:34]3[CH2:35][CH2:36][N:37]([C:40](=[O:42])[CH3:41])[CH2:38][CH2:39]3)=[CH:32][CH:33]=1)=[N:3][CH:4]=2)[CH2:14][CH3:15])[CH3:13]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 86637353HCID 86637353, compound

Product 1

HCID 58015888HCID 58015888, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 2-chloro-9-(1-ethyl-propyl)-9H-purine (90 mg, 0.4 mmol) and TsOH (1.6 mL, 0.2 M in 1,4-dioxane) in DMF (0.25 mL) is added 1-[4-(4-amino-phenyl)-piperazin-1-yl]-ethanone (105 mg, 0.5 mmol). The reaction mixture is sealed in a microwave reactor and heated at 140° C. for 30 min. The mixture is diluted with EtOAc and washed with NaHCO3 aqueous solution and brine. The organics are dried over Na2SO4, filtered and concentrated. The crude product is purified by preparative HPLC to give 40 mg of 1-(4-{4-[9-(1-ethyl-propyl)-9H-purin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone.

Workup

  1. customThe reaction mixture is sealed in a microwave reactor
  2. washwashed with NaHCO3 aqueous solution and brine
  3. dry with materialThe organics are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-b9f191be14d34001afb9be8c46a1c5f8
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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