o-(1-Piperazinyl)phenol → HCID 10167622, compound

Participants

Reaction Steps

1-[3-(4-Iodo-phenyl)-1-oxiranylmethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone (62 mg, 0.15 mmol) and 4-(2-hydroxyphenyl)-piperazine (34 mg, 0.19 mmol) were combined in CH2Cl2 (0.5 mL) and the solution treated with Yb(OTf)3.H2O (44 mg, 0.071 mmol). The mixture was shaken for 72 h then diluted with CH2Cl2 (1 mL). Purification by preparative TLC (silica, 10% MeOH/CH2Cl2) grave 45 mg (51%) of an off-white powder. TLC (silica, 8% MeOH/CH2Cl2): Rf=0.2. MS (electrospray): m/z calculated for C27H33IN5O3 [M+H]+ 602.15, found 602.2. 1H NMR (CDCl3, 500 MHz, a mixture of amide rotamers): 7.76 (d, J=8.6 Hz,1H), 7.72 (d, J=8.6 Hz, 1H), 7.42 (d, J=8.5 Hz, 1H), 7.34 (d, J=8.5 Hz, 1H), 7.14 (m, 1H), 7.80 (t, J=7.7 Hz, 1H), 6.94 (d, J=8.1 Hz, 1H), 6.86 (t, J=7.7 Hz, 1H), 4.83 and 4.72 (A and B of AB quartet, Jab=15.6 Hz, 1H), 4.61 (s, 1H), 4.22-4.15 (m, 2H), 4.02 (m, 2H), 3.88 (m, 1H), 3.76 (m, 3H), 3.00-2.49 (m, 11H), 2.20 (s, 1.5H), 2.15 (s, 1.5H).

Provenance & Evidence