HCID 136374693, compound → HCID 136186317, compound

HRID 1467773Notes

Reaction equation

HRID 1467773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3=[N:14][NH:15][C:16](=[O:21])[C:17]4[CH:18]=[CH:19][CH:20]=[C:11]([C:12]=43)[NH:10][CH:9]2[C:22]2[CH:27]=[CH:26][C:25]([CH:28]3[CH2:32][CH2:31][CH2:30][N:29]3C(OCC3C=CC=CC=3)=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:13]3=[N:14][NH:15][C:16](=[O:21])[C:17]4[CH:18]=[CH:19][CH:20]=[C:11]([C:12]=43)[NH:10][CH:9]2[C:22]2[CH:27]=[CH:26][C:25]([CH:28]3[CH2:32][CH2:31][CH2:30][NH:29]3)=[CH:24][CH:23]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 136374693HCID 136374693, compound

Product 1

HCID 136186317HCID 136186317, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 2-(4-(9-(4-fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)phenyl)pyrrolidine-1-carboxylate (60 mg, 0.107 mmol) was dissolved in distilled methanol (15 mL), and the reaction mixture was stirred at room temperature under an atmosphere of hydrogen in the presence of a catalytic amount of palladium on carbon (11 mg, 0.01 mmol) for 2 hrs. After the reaction was completed, the catalyst was removed by filtration through a pad of Celite, and the solvent was removed under reduced pressure. The residue was purified by preparative TLC (MeOH:DCM=1:10) to give the title compound (5 mg, yield 11%) as a white foam. LC-MS (ESI) m/z: 426 (M+1)+ 1H-NMR (400 MHz, CD3O) δ (ppm): 1.78-1.88 (m, 1H), 1.95-2.08 (m, 2H), 2.24-2.32 (m, 1H), 3.05-3.12 (m, 1H), 3.21-3.27 (m, 1H), 4.17-4.21 (m, 1H), 4.34-4.36 (d, J=8.0 Hz, 1H), 4.75-4.77 (d, J=8.0 Hz, 1H), 6.91-6.95 (m, 2H), 7.09-7.15 (m, 2H), 7.17-7.25 (m, 1H), 7.22-7.25 (m, 1H), 7.29-7.34 (m, 4H), 7.55-7.57 (m, 1H), 7.63-7.67 (m, 1H).

Workup

  1. customthe catalyst was removed by filtration through a pad of Celite
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by preparative TLC (MeOH:DCM=1:10)

Sources & evidence

ORD record
ord-5b161e0c28794d23af6878899d39825a
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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