p-Toluenesulfonic acid → HCID 24855622, compound

HRID 2189340Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([NH:6][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.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][N:38]([C:41](=[O:43])[CH3:42])[CH2:37][CH2:36]2)=[CH:31][CH:30]=1>CN(C=O)C.CCOC(C)=O>[C:41]([N:38]1[CH2:37][CH2:36][N:35]([C:32]2[CH:33]=[CH:34][C:29]([NH:28][C:2]3[N:10]=[C:9]4[C:5]([NH:6][C:7](=[O:16])[N:8]4[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:4][N:3]=3)=[CH:30][CH:31]=2)[CH2:40][CH2:39]1)(=[O:43])[CH3:42]

Participants

Conditions

Temperature: 140 °C

Procedure

To a mixture of 2-chloro-9-(1-ethyl-propyl)-7,9-dihydro-purin-8-one (95 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 organic layer is dried over Na2SO4, filtered and concentrated. The crude product is purified by preparative HPLC to give 52 mg of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-9-(1-ethyl-propyl)-7,9-dihydro-purin-8-one as a brown solid.

Workup

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

Sources & evidence

ORD record: ord-a3108a0ecab84559bcf4e1e2aa294568
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324225B2

Reaction notes

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