Trifluoroacetic acid → HCID 178523012, compound

HRID 571405Notes

Reaction equation

[CH:1]1([C:4]2[C:8]3[CH:9]=[N:10][C:11]([NH:13][C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)=[O:15])=[CH:12][C:7]=3[N:6](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:5]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>>[CH:1]1([C:4]2[C:8]3[CH:9]=[N:10][C:11]([NH:13][C:14]([NH:16][CH2:17][C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)=[O:15])=[CH:12][C:7]=3[NH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 895259191-(3-cyclopropyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(4-fluorobenzyl)urea

Product 1

HCID 178523012HCID 178523012, compoundYield 42.5%

Procedure

A mixture of 1-(3-cyclopropyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(4-fluorobenzyl)urea (70 mg, 0.123 mmol), TFA (1900 24.66 mmol), and triethylsilane (19.70 μl, 0.123 mmol) was stirred at room temperature. The reaction was concentrated, taken up in DMSO (2 mL) and purified by preparative HPLC (Reverse phase C-18, Waters SunFire PrepODB, 150×19 mm, 5u, eluting with 10-95% Acetonitrile/Water+0.1% TFA (20 mL/min) over 10 min.) to give 1-(3-cyclopropyl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(4-fluorobenzyl)urea (23 mg, 0.052 mmol, 42.5% yield) as an off-white solid. MS ESI calc'd. for C17H16FN5O [M+1]+ 326, found 326.

Workup

concentrationThe reaction was concentrated
custompurified by preparative HPLC (Reverse phase C-18, Waters SunFire PrepODB, 150×19 mm, 5u, eluting with 10-95% Acetonitrile/Water+0.1% TFA (20 mL/min) over 10 min.)

Sources & evidence

ORD record: ord-cacd8e95574b40ae8d5c607e9758834f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023865B2

Reaction notes

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