Trifluoroacetic acid → Trifluoroacetic acid

HRID 1522579Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][N:24](COCC[Si](C)(C)C)[C:17]=23)[CH:12]=[CH:11][N:10]=1.FC1C=CC(F)=CC=1C1C=C(NC2C3C(=CN(COCC[Si](C)(C)C)N=3)N=CC=2)C=CN=1.[F:65][C:66]([F:71])([F:70])[C:67]([OH:69])=[O:68]>C1(OC)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][NH:24][C:17]=23)[CH:12]=[CH:11][N:10]=1.[C:67]([OH:69])([C:66]([F:71])([F:70])[F:65])=[O:68]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of N-(2-(2,5-difluorophenyl)pyridin-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(2-(2,5-difluorophenyl)pyridin-4-yl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-pyrazolo[4,3-b]pyridin-7-amine (1.2 g, 3.2 mmol) were combined with trifluoroacetic acid (1.1 mL) and stirred at 70° C. for 15 minutes. Anisole (20 μL) was then added and the mixture was further heated at 70° C. The reaction mixture was then purified via preparative HPLC using a gradient of 10-30% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 75×30 mm column to give the title compound as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.39-7.52 (m, 4H) 7.79 (br. s., 2H) 7.95 (s, 1H) 8.57 (d, J=6.32 Hz, 2H) 8.76 (br. s., 2H). MS [M+H] found 324.2.

Workup

temperaturethe mixture was further heated at 70° C
customThe reaction mixture was then purified via preparative HPLC

Sources & evidence

ORD record: ord-cefd6134dc4f47169156c46c51909e8a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073918B2

Reaction notes

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