p-Toluenesulfonic acid → HCID 24855622, compound

HRID 2189342Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6](C)[C:7](=[O:16])[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.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][N:39]([C:42](=[O:44])[CH3:43])[CH2:38][CH2:37]2)=[CH:32][CH:31]=1>CN(C=O)C.CCOC(C)=O>[C:42]([N:39]1[CH2:38][CH2:37][N:36]([C:33]2[CH:34]=[CH:35][C:30]([NH:29][C:2]3[N:10]=[C:9]4[C:5]([NH:6][C:7](=[O:16])[N:8]4[CH:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[CH:4][N:3]=3)=[CH:31][CH:32]=2)[CH2:41][CH2:40]1)(=[O:44])[CH3:43]

Participants

Conditions

Temperature: 140 °C

Procedure

To a mixture of 2-chloro-9-(1-ethyl-propyl)-7-methyl-7,9-dihydro-purin-8-one (102 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 50 mg of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-9-(1-ethyl-propyl)-7,9-dihydro-purin-8-one.

Workup

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

Sources & evidence

ORD record: ord-895b381a0ae84f1b87a8e39320aafd90
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324225B2

Reaction notes

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