Diisopropylethylamine → 4-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-(4-hydroxybenzyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Hydroxybenzylamine	HCID 97472	—
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	4-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino) benzoic acid	HCID 58228829	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-(4-hydroxybenzyl)benzamide	HCID 59023056	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A mixture of 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino) benzoic acid (116 mg, 0.35 mmol), 4-aminomethylphenol (43 mg, 0.35 mmol), and N,N-diisopropylethylamine (0.094 mL, 0.525 mmol) in DMF (1 mL) is cooled to 0° C., and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (160 mg, 0.42 mmol) is added. The cooling bath is removed, and the reaction mixture stirred at 25° C. for 18 hours. After this time the solvent is removed in vacuo, and the residue triturated with MeOH. The resultant solid is collected by filtration and identified as the desired phenol.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07893058B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-f8651e00e6994c8fa30a2df87b070da8
Source note	uspto-grants-2011_02