O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 67064333, compound

Participants

Reaction Conditions

Reaction Steps

7-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9A, 110 mg, 0.50 mmol) and 4-(1-(methoxycarbonyl)cyclopropyl)benzoic acid (110 mg, 0.50 mmol) were mixed in pyridine (3 ml). TBTU (160 mg, 0.50 mmol) was then added and the mixture was heated to 80° C. for 15 hours. After cooling to room temperature, additional TBTU (53 mg, 0.17 mmol) was added before the heating continued for another 6 hours. After cooling to room temperature, the reaction mixture was quenched with water and was then concentrated to dryness in vacuo. The crude product was purified by preparatory HPLC (35-55% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white powder (72 mg, 35% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.00 (s, 1H), 8.10 (d, J=2.3 Hz, 1H), 7.99 (d, J=8.3 Hz, 2H), 7.49 (d, J=8.3 Hz, 2H), 7.41 (s, 1H), 6.38 (d, J=2.3 Hz, 1H), 3.88-3.82 (m, 4H), 3.78-3.70 (m, 4H), 3.57 (s, 3H), 1.56-1.50 (m, 2H), 1.30-1.24 (m, 2H); ESI-MS: m/z 422.4 (M+H)+.

Provenance & Evidence