4,4,4-Trifluorobutylamine → 2-[5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-4-[(4,4,4-trifluorobutyl)amino]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 536507

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[C:13](I)[C:14]4[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=4[N:16]=3)=[N:9][N:8]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[C:5]2=[N:6][CH:7]=1.[F:32][C:33]([F:39])([F:38])[CH2:34][CH2:35][CH2:36][NH2:37]>CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[C:13]([NH:37][CH2:36][CH2:35][CH2:34][C:33]([F:39])([F:38])[F:32])[C:14]4[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=4[N:16]=3)=[N:9][N:8]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

150 mg (0.186 mmol, approx. 66% purity) of the compound obtained in example 16A was dissolved in 1-methyl-2-pyrrolidone (3 ml) in a reaction vessel suitable for a microwave and 0.4 ml of 4,4,4-trifluorobutylamine was added. Then it was sealed with a corresponding septum and it was heated in the microwave at 150° C. for 3 h. After cooling, the reaction mixture was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 47 mg of the title compound was obtained (48% of theor.).

Workup

additionwas added
customThen it was sealed with a corresponding septum and it
temperatureAfter cooling
customthe reaction mixture was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record: ord-2e264ea1807446199134889ce89898ed
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859569B2

Linked notes

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