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

HRID 970097Notes

Reaction equation

HRID 970097 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16][C:11]=3[N:10]([CH2:20][CH:21]3[CH2:23][O:22]3)[N:9]=2)=[CH:4][CH:3]=1.[OH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>C(Cl)Cl>[OH:22][CH:21]([CH2:23][N:34]1[CH2:33][CH2:32][N:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[OH:24])[CH2:36][CH2:35]1)[CH2:20][N:10]1[C:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[CH2:13][C:12]=2[C:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)=[N:9]1

Participants

5

Reactant 3

HCID 70530o-(1-Piperazinyl)phenolHCID 11452972HCID 11452972, compoundHCID 45075687Ytterbium(3+) trifluoromethanesulfonate--water (1/3/1)

Product 1

HCID 10167622HCID 10167622, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  1. customPurification by preparative TLC (silica, 10% MeOH/CH2Cl2) grave 45 mg (51%) of an off-white powder

Sources & evidence

ORD record
ord-cc109207c8f84365b2c94b4109e79f84
Source dataset
uspto-grants-2007_12
Patent number
US07309703B2

Reaction notes

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