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

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
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-[(2-Methoxyethoxy)methyl]-5-(pentafluoro-lambda6-sulphanyl)benzoic acid	HCID 89699667	—
Reactant	HCID 89699939	HCID 89699939	—
Product	N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-[(2-methoxy-ethoxy)methyl]-5-(pentafluoro-lambda6-sulphanyl)benzamide	HCID 71667404	—

Reaction Steps

58 mg (0.173 mmol) of the compound of Example 98A and 75 mg (0.198 mmol) of HATU were dissolved in 1 ml of DMF, and 24 mg (0.198 mmol) of 4-N,N-dimethylaminopyridine (DMAP) were added slowly. 50 mg (0.165 mmol) of the compound of Example 11A were then added. The reaction mixture was stirred at RT for about 16 h and then separated into its components by preparative HPLC (Method 36). Pooling of the product fractions, evaporation and drying of the residue under high vacuum gave 76 mg (75% 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-965cf988baa345b2bb41fa2a34eaa54d
Source note	uspto-grants-2016_07