Ethylenediamine → HCID 71287857, Verbindung

In a 25 mL round-bottomed flask, 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-hydroxycyclohexyl)amide (106 mg, 0.19 mmol) was dissolved dichloromethane (3 mL). Trifluoroacetic acid (0.2 mL, 2.6 mmol) was added and the orange reaction mixture was stirred at room temperature for 15 h. Additional trifluoroacetic acid (0.7 mL) was added and the reaction stirred for an additional 5 h. The reaction mixture was then concentrated under reduced pressure. The resultant crude solid was dissolved in dichloromethane (3 mL) and ethylenediamine (0.20 mL, 2.96 mmol) was added. The light yellow reaction mixture was stirred at room temperature for 20 h. The reaction mixture was concentrated and the residue was precipitated with water. The suspension was stirred for 1 h and the crude solid collected by filtration. The crude solid was sequentially washed with water, dichloromethane, ethyl acetate, and hexanes to afford 74 mg (91%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-hydroxy-cyclohexyl)-amide as a white solid and a 2:1 mixture of cis and trans isomers (unassigned). MS: [M+Na] 447.

1. stirringthe reaction stirred for an additional 5 h
2. concentrationThe reaction mixture was then concentrated under reduced pressure
3. dissolutionThe resultant crude solid was dissolved in dichloromethane (3 mL)
4. stirringThe light yellow reaction mixture was stirred at room temperature for 20 h
5. concentrationThe reaction mixture was concentrated
6. customthe residue was precipitated with water
7. stirringThe suspension was stirred for 1 h
8. filtrationthe crude solid collected by filtration
9. washThe crude solid was sequentially washed with water, dichloromethane, ethyl acetate, and hexanes

ORD-Eintrag

ord-2eba6e019f10412ea9c3498baea6e75f

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08658646B2