4-Methylmorpholine → HCID 49841212, compound

https://huagongshe.com/reaction/1968287

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Aminoacetonitrile	HCID 10901	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	Pyrrolo[4,3,2-de][2,6]naphthyridine-4(3H)-acetic acid, α-(1,1-dimethylethyl)-1,5-dihydro-3-oxo-, (αR)-	HCID 58293442	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 49841212	HCID 49841212	79.6%

Reaction Steps

(R)-3,3-Dimethyl-2-(3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)butanoic acid (40.0 mg, 0.139 mmol), HOBt hydrate (25.6 mg, 0.167 mmol), and EDC hydrochloride (40.0 mg, 0.209 mmol) were combined in DMF (2 mL). 2-Aminoacetonitrile (11.71 mg, 0.209 mmol) and 4-methylmorpholine (0.062 mL, 0.557 mmol) were added, and the reaction mixture was stirred at room temperature for 2 h. The product was purified by preparative HPLC (10-45% AcCN/H2O with 0.035% TFA), concentrated in vacuo, and lyophilized to afford the title compound as a pale yellow solid (36 mg, 59%). 1H NMR (500 MHz, DMSO-d6) δ 1.09 (s, 9H), 4.01-4.12 (m, 2H), 5.13-5.22 (m, 2H), 5.33 (br s, 1H), 7.10 (d, J=4.5 Hz, 1H), 7.87 (s, 1H), 8.26 (d, J=4.5 Hz, 1H), 8.86 (br s, 1H), 12.25 (br s, 1H). [M+H] calc'd for C17H19N5O2, 326; found, 326.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08420816B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-0aaf1348173148e5a900d2c8cb5046e7
Source note	uspto-grants-2013_04