Hydrochloric Acid → methyl 2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)acetate

HRID 402480

Reaction equation

Br[C:2]1[N:7]=[C:6]2[N:8]([CH3:17])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]2=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].Cl.[CH3:29][O:30][C:31](=[O:34])[CH2:32][NH2:33]>CN(C=O)C>[CH3:17][N:8]1[C:6]2=[N:7][C:2]([NH:33][CH2:32][C:31]([O:30][CH3:29])=[O:34])=[CH:3][C:4]([C:18]([F:21])([F:20])[F:19])=[C:5]2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred mixture of 6-bromo-1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (0.15 g, 0.422 mmol) and Na2CO3 (0.135 g, 1.267 mmol) in dry DMF (6.0 mL), glycine methylester×HCl (0.08 g, 0.633 mmol) was added at it and heated to 100° C. for 6 h. The reaction mixture was cooled to it and poured into rapidly stirred ice cold water. The crude compound was extracted with EtOAc and purified by column chromatography (eluent: 10% EtOAc in hexane) to yield the title compound as a colorless solid (0.05 g, 32%). [1H-NMR (CDCl3, 300 MHz) δ 7.55-7.38 (m, 5H), 6.68 (s, 1H), 5.42 (t, 1H), 4.32 (d, 2H), 4.05 (s, 3H), 3.75 (s, 3H); LCMS RtC=0.469 min; [M+H]+=364.8]

Workup

additionwas added at it
temperatureThe reaction mixture was cooled to it
additionpoured into rapidly stirred ice cold water
extractionThe crude compound was extracted with EtOAc
custompurified by column chromatography (eluent: 10% EtOAc in hexane)

Sources & evidence

ORD record: ord-929f906dc1694cd1887310cfeb9ecb8a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742106B2

Linked notes

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