Water → HCID 86344808, compound

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Tetrabutylammonium Fluoride	HCID 2724141	—
Reactant	1-[5-tert-Butyl-2-(3-chloro-4-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-1-methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea	HCID 123302085	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 86344808	HCID 86344808	68.1%

Reaction Steps

A solution of Intermediate 50a (280 mg, 0.345 mmol) and TBAF (1M in THF, 0.41 mL, 0.41 mmol) in THF (3 mL) was stirred at RT for 0.5 h. Water was added and the mixture extracted with DCM (3×15 mL). The combined organics were concentrated in vacuo. The residue was purified by FCC, using 0-14% MeOH in DCM, to give the title compound (154 mg, 68%). LCMS (Method 5): Rt 3.52 min, m/z 655.2 [MH+]. 1H NMR (400 MHz, d6-DMSO): 1.26 (9H, s), 1.82-2.26 (11H, m), 2.31-2.39 (1H, m), 3.10-3.16 (1H, m), 3.99 (1H, d, J=8.2 Hz), 4.77-4.85 (1H, m), 5.35-5.42 (1H, m), 6.28 (1H, s), 7.03-7.10 (2H, m), 7.22-7.38 (6H, m), 7.43 (1H, d, J=2.5 Hz), 7.75 (1H, dd, J=9.9 Hz), 7.99 (1H, s), 8.24 (1H, br d), 10.56 (1H, v br).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440974B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-06ce7fc2024043d3bfa4c7e865d2e2d1
Source note	uspto-grants-2016_09