Phenylacetic Acid → N-[4-(morpholin-4-yl)-1-oxophthalazin-2(1H)-yl]-2-phenylacetamide

https://huagongshe.com/en/reaction/535539

Participants

Role	Name	HCID	Charge
Reactant	Phenylacetic Acid	HCID 999	—
Reactant	Triethylamine	HCID 8471	—
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	2-amino-4-morpholinophthalazin-1(2H)-one	HCID 70976104	—
Product	N-[4-(morpholin-4-yl)-1-oxophthalazin-2(1H)-yl]-2-phenylacetamide	HCID 70976253	—

Reaction Steps

To a 4 mL vial was added the product from Example 1B (20 mg in dimethyl acetamide), phenylacetic acid [1.5 equivalents in dimethyl acetamide], O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 2 equivalents in dimethyl acetamide) and triethylamine (3 equivalents, neat). The vial was capped and microwaved at 150° C. for 30 minutes. The reaction was checked by LC/MS and concentrated to dryness upon completion. The residue was dissolved in 1:1 MeOH:DMSO and purified by reverse phase HPLC (conditions from Example 10C): 1H NMR (500 MHz, DMSO-d6/D2O) δ 8.33-8.28 (m, 1H), 8.03 (d, J=7.5, 1H), 8.01-7.96 (m, 1H), 7.94-7.87 (m, 1H), 7.40-7.33 (m, 4H), 7.33-7.25 (m, 1H), 3.86-3.78 (m, 4H), 3.67 (s, 2H), 3.11-3.06 (m, 4H); MS (ESI+) M/Z 365 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08859549B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-18bf992b4f04433fac641294f2b4bc7e
Source note	uspto-grants-2014_10