1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59755964, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of resin B (1.2 mmol/g, 5.0 g, 8.0 mmol) in pyridine (12 mL) was added dimethyl-pyrrolidin-3-yl-amine (1.37 mL, 12 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 2.2 mL, 14.4 mmol) at room temperature. The mixture was agitated at 100° C. for 12 hours under a nitrogen atmosphere. The resin was washed with DCM then MeOH (3×), and dried under vacuum. Compound C was cleaved off the resin with the addition of 50% trifluoroacetic acid in DCM. The mixture was agitated at room temperature for 30 minutes. The resin was washed with DCM (3×), and the filtrate was concentrated using a rotary evaporator. 1 N HCl aqueous solution (2 mL) was added and then lyophilized to yield compound C as a light pink gum (2.2 g). The compound was taken onto the next step without further purification. 1H-NMR δ (CDCl3): 10.85 (s, 1H), 8.26 (dd, 1H, J=4.8 Hz, J=1.6 Hz), 7.96 (dd, 1H, J=7.2 Hz, J=2.0 Hz), 6.81 (dd, 1H, J=7.6 Hz, J=4.8 Hz), 3.92-3.94 (m, 1H), 3.70-3.80 (m, 2H), 3.52-3.54 (m, 1H), 3.43 (m, 1H), 2.80 (m, 6H), 2.20 (m, 1H), 2.17 (m, 1H). ESMS: 236.0 [M+H]+.

Provenance & Evidence