2-Amino-5-bromo-N-methylbenzamide → 2-Amino-5-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	2-Amino-5-bromo-N-methylbenzamide	HCID 50999511	—
Reactant	4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-ol	HCID 67814792	—
Reactant	2-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide	HCID 86697680	—
Product	2-Amino-5-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylbenzamide	HCID 67812465	17%

Reaction Steps

Prepared analogously to Compound 3C using 2-amino-5-bromo-n-methyl-benzamide (Compound 8D, 300 mg, 1.31 mmol) and 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-ol (Compound 14C, 383 mg, 1.44 mmol) to afford 64 mg of the title compound (17%). 1H NMR (400 MHz, CDCl3) δ 7.67 (s, 1H), 7.54 (s, 1H), 7.40 (d, J=2.0 Hz, 1H), 7.32 (dd, J=2.0, 8.6 Hz, 1H), 6.71 (d, J=8.3 Hz, 1H), 6.13 (br. s., 1H), 5.43 (br. s., 2H), 4.20 (t, J=6.9 Hz, 2H), 3.65-3.72 (m, 2H), 3.01 (d, J=5.1 Hz, 3H), 2.01 (quin, J=7.3 Hz, 2H), 1.58-1.67 (m, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133224B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-78aca5222e604fa9aa98419560da2d48
Source note	uspto-grants-2015_09