HCID 178474107, compound → HCID 178474106, compound

HRID 1433157Notes

Reaction equation

HRID 1433157 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([N:16]3[CH2:21][CH2:20][N:19](C(OCC4C=CC=CC=4)=O)[CH2:18][CH2:17]3)=[CH:14][NH:13][N:12]=2)=[C:7]([O:32]CC2C=CC=CC=2)[CH:6]=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([N:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)=[CH:14][NH:13][N:12]=2)=[C:7]([OH:32])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 178474107HCID 178474107, compound

Product 1

HCID 178474106HCID 178474106, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-[4-acetamido-2-benzyloxyphenyl]-4-[4-(benzyloxycarbonyl)piperazin-1-yl]-1H-pyrazole (70 mg, 133.2 μmol) in MeOH (7 mL) was degassed (3× vacuum/nitrogen) and palladium (10% on carbon; 10 mg, cat.) added. The reaction mixture was again degassed (3× vacuum/nitrogen) and the atmosphere replaced with one of hydrogen (3× vacuum/hydrogen). The mixture was shaken at room temperature for 18 hours. The catalyst was removed by filtration through a small pad of celite and washed with further MeOH (15 mL). The solvent was removed in vacuo to give crude product, which was purified by preparative HPLC to give 3-[4-acetamido-2-hydroxyphenyl]-4-(piperazin-1-yl)-1H-pyrazole (16.3 mg, 41%) as a white solid; δH (MeOH-d4) 8.47 (1H, s), 7.80 (1H, br s), 7.68 (1H, s), 7.26 (1H, s), 7.11 (1H, dd, J=8.5, 2.1 Hz), 3.34-3.29 (4H, m), 3.11-3.07 (4H, m), 2.12 (3H, s); LCMS retention time 1.26 min, M+H+ 302.3.

Workup

  1. additionadded
  2. customThe reaction mixture was again degassed (3× vacuum/nitrogen)
  3. customThe catalyst was removed by filtration through a small pad of celite
  4. washwashed with further MeOH (15 mL)
  5. customThe solvent was removed in vacuo
  6. customto give crude product, which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-9b393b8ee19c4a5aa8679917ab8eaf3c
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

Loading…