Borane → HCID 67460150, compound

To a solution of 4-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)-2-chlorobenzoic acid (1.15 g, 75% purity, 2.9 mmol) in THF (6.0 mL) at 0° C. under N2 was added a solution of borane in THF (1.0 M, 11.7 mL, 11.7 mmol) over 5 min and the reaction mixture warmed to RT for 6 hr. An additional aliquot of the borane solution (3.0 mL, 3.0 mmol) was added and the reaction mixture maintained at RT for a further 18 hr, then quenched by the addition of MeOH (30 mL) and after 10 min at RT was evaporated in vacuo. The residue was partitioned between DCM (20 mL) and brine (10 mL). The aq layer was separated and was extracted with DCM (10 mL) and the combined organic layers were dried and evaporated in vacuo to afford 3-(tert-butyl)-1-(3-chloro-4-(hydroxymethyl)phenyl)-1H-pyrazol-5-amine as a dark orange oil (1.15 g, 70% purity, 98%); Rt 3.92 min (Method 1 basic); m/z 280 (M+H)+, (ES+). This material was used in the subsequent step without further purification

1. temperaturethe reaction mixture maintained at RT for a further 18 hr
2. customquenched by the addition of MeOH (30 mL) and after 10 min at RT
3. customwas evaporated in vacuo
4. customThe residue was partitioned between DCM (20 mL) and brine (10 mL)
5. customThe aq layer was separated
6. extractionwas extracted with DCM (10 mL)
7. customthe combined organic layers were dried
8. customevaporated in vacuo

ORD record

ord-7b753684a76940d2928675c1fc01a4dd

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024041B2