HCID 68153991, compound → HCID 69935372, compound

HRID 341103Notes

Reaction equation

HRID 341103 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:30](=[O:31])[C:11]2=[CH:12][N:13]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1>CO>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]3=[N:9][N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:30](=[O:31])[C:11]3=[CH:12]2)=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 68153991HCID 68153991, compound

Product 1

HCID 69935372HCID 69935372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Methylphenyl)-5-(4-nitrobenzyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 755, 50 mg, 0.12 mmol) was suspended in methanol (5 mL) and the mixture was sparged under an atmosphere of nitrogen. The mixture was treated with Raney Ni (˜20 mg, spatula tip) and sparged under an atmosphere of hydrogen (1 atm). The mixture was, stirred vigorously for 6 hours at ambient temperature, sparged under an atmosphere of nitrogen, filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, CD3OD) δ 8.96 (1H, s), 8.34 (1H, d, J=6.4 Hz), 7.82 (1H, d, J=8.6 Hz), 7.67-7.58 (2H, m), 7.44-7.36 (6H, m), 7.29 (2H, d, J=8.2 Hz), 5.82 (2H, s), 2.27 (3H, s), ppm; low resolution mass spectrometry (ES+) m/z 381.0 (M+H)+; calculated for C24H20N4O: 381.2].

Workup

  1. customthe mixture was sparged under an atmosphere of nitrogen
  2. additionThe mixture was treated with Raney Ni (˜20 mg, spatula tip)
  3. customsparged under an atmosphere of hydrogen (1 atm)
  4. customsparged under an atmosphere of nitrogen
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by preparative reverse phase HPLC (90:10 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d72d19e1605f485d9f41a887de6880ae
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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