3-(4-Bromo-pyrazol-1-yl)-3-methyl-butan-1-ol → 3-amino-6-[1-(4-hydroxy-2-methylbutan-2-yl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	3-(4-Bromo-pyrazol-1-yl)-3-methyl-butan-1-ol	HCID 67811274	—
Reactant	3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide	HCID 67818926	—
Reactant	2-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide	HCID 86697680	—
Product	3-amino-6-[1-(4-hydroxy-2-methylbutan-2-yl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide	HCID 86697787	43%

Reaction Steps

Prepared analogously to Compound 3C using 3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (Compound 48D, 649 mg, 2.34 mmol) and 3-(4-bromo-pyrazol-1-yl)-3-methyl-butan-1-ol (Compound 50D, 600 mg, 2.57 mmol) to afford 304 mg of the title compound (43%). 1H NMR (400 MHz, CD3OD) δ 8.34 (d, J=0.5 Hz, 1H), 8.01 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.15 (d, J=8.6 Hz, 1H), 3.40 (t, J=7.2 Hz, 2H), 2.94 (s, 3H), 2.17 (t, J=7.3 Hz, 2H), 1.66 (s, 6H). MS (ESI): m/z=304.26 [M+H]+. UPLC: tR=0.77 min (UPLC-TOF: polar—2 min).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133224B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-8a1b87eda39e4365bbee3d4dd707a525
Source note	uspto-grants-2015_09