N-Methylethylamine → 6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-((ethyl(methyl)amino)methyl)pyrimidin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	N-Methylethylamine	HCID 12219	—
Reactant	4-Amino-6-{4-[1-(2-dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbaldehyde	HCID 89442719	—
Solvent	1,2-Dichloroethane	HCID 11	—
Product	6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-((ethyl(methyl)amino)methyl)pyrimidin-4-amine	HCID 89442749	—

Reaction Steps

To a solution of 4-Amino-6-{4-[1-(2-dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbaldehyde (90.00 mg; 0.18 mmol; 1.00 eq.) in 1 ml DCE added ethyl-methyl-amine (0.02 ml; 0.19 mmol; 1.05 eq.) and sodium p-triacetoxyborohydride (113.20 mg; 0.53 mmol; 3.00 eq.), stirred for overnight at RT, lc-ms showed desired (<30%, major ms 618/619), purified by prep HPLC, collected title compound. LC-MS: (M+1=549, obsd.=549).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09145392B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-f68509765e194071baf5c304d83094d6
Source note	uspto-grants-2015_09