Diisopropylethylamine → 3-Hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	3-Hydroxy-5-(pentafluorosulfanyl)benzoic acid	HCID 58136794	—
Reactant	4-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline	HCID 89700023	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-Hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide	HCID 89700329	—

Reaction Steps

300 mg (1.04 mmol) of the compound of Example 6A, 301 mg (1.14 mmol) of the compound of Example 24A and 473 mg (1.24 mmol) of HATU were initially charged in 3.6 ml of DMF, 0.36 ml (2.07 mmol) of N,N-diisopropylethylamine was added and the mixture was stirred at RT for two days. The reaction was then directly separated into its components by preparative HPLC (Method 18). This gave 180 mg (31% of theory) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09394309B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-873263a4469f4703ad6afe5b899a3660
Source note	uspto-grants-2016_07