Hydrochloric Acid → (R)-1-(3-(ethylamino)-7-fluoro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 590810Notes

Reaction equation

[CH2:1]([N:3]([C:7]1[C:11]2[CH:12]=[N:13][C:14]([NH:17][C:18]([NH:20][C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])=[O:19])=[C:15]([F:16])[C:10]=2[NH:9][N:8]=1)C(=O)C)[CH3:2].Cl>C1COCC1>[CH2:1]([NH:3][C:7]1[C:11]2[CH:12]=[N:13][C:14]([NH:17][C:18]([NH:20][C@@H:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH3:22])=[O:19])=[C:15]([F:16])[C:10]=2[NH:9][N:8]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

(R)—N-Ethyl-N-(7-fluoro-6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide (27 mg, 0.070 mmol) was dissolved in THF (3 mL), charged with HCl (300 μL, 3.65 mmol), and heated to 60° C. for 4 h. The solvents were removed in vacuo and the residue was taken up in DMF and purified by mass-triggered reverse phase HPLC. Fractions containing pure compound were filtered through a PS-HCO3 cartridge and the filtrate was concentrated in vacuo to give (R)-1-(3-(ethylamino)-7-fluoro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C17H19FN6O [M+1]+ 343. found 343. 1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.67 (s, 1H), 8.90 (br s, 1H), 8.49 (s, 1H), 7.39-7.27 (m, 4H), 7.26-7.18 (m, 1H), 4.90 (t, J=7.2 Hz, 1H), 3.25 (m, 2H), 1.42 (d, J=6.9 Hz, 3H), 1.20 (t, J=7.2 Hz, 3H).

Workup

customThe solvents were removed in vacuo
custompurified by mass-triggered reverse phase HPLC
additionFractions containing pure compound
filtrationwere filtered through a PS-HCO3 cartridge
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-0b1d03483bbd4184bc4270f85ad9047f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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