4-Methylmorpholine → HCID 11247409, compound

https://huagongshe.com/reaction/2075471

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-	HCID 85083	—
Reactant	Tetrafluoro-m-phenylenediamine dihydrochloride	HCID 149026	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanone	HCID 11427553	—
Reactant	Hydrochloride methanol	HCID 21893726	—
Solvent	Methanol	HCID 887	—
Product	HCID 11247409	HCID 11247409	20%

Reaction Conditions

Temperature	60 °C

Reaction Steps

The product obtained using dihydrochloride of Compound 18 (100 mg, 0.25 mmol), N-(tert-butoxycarbonyl)-L-proline (53 mg, 0.25 mmol), 1-hydroxybenzotriazole monohydrate (43 mg, 0.33 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (66 mg, 0.35 mmol) and N-methylmorpholine (0.06 mL, 0.50 mmol) in a similar manner to Example 5, was dissolved in methanol (2.00 mL), and the solution was added with 4 mol/L hydrogen chloride-methanol solution (1.50 mL) followed by heating under reflux at 60° C. for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was added with saturated sodium hydrogencarbonate solution and ethyl acetate, followed by extraction. The crude product was crystallized from acetone to obtain Compound 140 (21 mg, 20%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07919517B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-3fbce1c0c4404f2da8f026c5218c40ad
Source note	uspto-grants-2011_04