p-Toluenesulfonic acid → N2-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N6-(2-(isopropylsulfonyl)phenyl)-7-methyl-7H-purine-2,6-diamine

HRID 2046998Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH3:11])[CH:7]=[N:8]2)=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[N:3]=1.[CH:25]([O:28][C:29]1[CH:35]=[C:34]([CH:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:33]([CH3:43])=[CH:32][C:30]=1[NH2:31])([CH3:27])[CH3:26].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[CH:25]([O:28][C:29]1[CH:35]=[C:34]([CH:36]2[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]2)[C:33]([CH3:43])=[CH:32][C:30]=1[NH:31][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH3:11])[CH:7]=[N:8]2)=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[N:3]=1)([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2-chloro-N-(2-(isopropylsulfonyl)phenyl)-7-methyl-7H-purin-6-amine (1 equivalent) in isopropanol, was added 2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)aniline (1 equivalent) and 4-methylbenzenesulfonic acid (1 equivalent). The suspension was stirred at 150° C. for 3 hours, cooled to room temperature and the solvent evaporated. The residue was purified using a preparative HPLC to afford the desired product as a gummy solid.

Workup

temperaturecooled to room temperature
customthe solvent evaporated
customThe residue was purified

Sources & evidence

ORD record: ord-8329caf415e346039efed7822a46eeb6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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