Azetidine → 6-(Azetidin-1-yl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-methyl-7,9-dihydro-8H-purin-8-one

HRID 510118Notes

Reaction equation

[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:22]=[C:21]3[C:17]([N:18]([CH3:24])[C:19](=[O:23])[NH:20]3)=[C:16](I)[N:15]=2)=[N:6]1.[NH:30]1[CH2:33][CH2:32][CH2:31]1>CN1CCCC1=O>[N:30]1([C:16]2[N:15]=[C:14]([C:7]3[C:8]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[N:5]([CH2:4][C:3]4[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=4[F:1])[N:6]=3)[N:22]=[C:21]3[C:17]=2[N:18]([CH3:24])[C:19](=[O:23])[NH:20]3)[CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 150 °C

Procedure

200 mg (0.399 mmol) of the compound obtained in example 107 were dissolved in N-methylpyrrolidone (3 ml) and admixed with 1.00 g (17.514 mmol) of azetidine, and then heated in a microwavable flask with septum in a microwave at 150° C. for 5 h. The mixture was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 9 mg of the title compound were obtained (5% of theory).

Workup

customThe mixture was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record: ord-2dd36de19b6b426391d8c5d1eaabbe84
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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