4-Methylmorpholine → 3-tert-Butyl-N-(3-{6-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylphenyl)-5-(4-methylpiperazin-1-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Sodium Hydroxide	HCID 14798	—
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-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylaniline trifluoroacetate	HCID 89700026	—
Reactant	3-tert-Butyl-5-(4-methylpiperazin-1-yl)benzoic acid trifluoroacetate	HCID 89700131	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-tert-Butyl-N-(3-{6-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylphenyl)-5-(4-methylpiperazin-1-yl)benzamide	HCID 89699798	—

Reaction Steps

65 mg (0.13 mmol) of the compound of Example 8A, 50 mg (0.13 mmol) of the compound of Example 21A and 58 mg (0.15 mmol) of HATU were dissolved in 0.73 ml of DMF, 0.07 ml (0.63 mmol) of 4-methylmorpholine was added and the mixture was stirred at RT for 16 h. 10 ml of 0.1 M aqueous sodium hydroxide solution were then added, and the mixture was stirred at RT for another 10 min. The precipitate formed was filtered off, washed with water and dried under high vacuum. This gave 70 mg (76% pure, 64% 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-ce50c68d8223493abb2f064faca2495d
Source note	uspto-grants-2016_07