HCID 136385312, compound → HCID 136053646, compound

HRID 1467534Notes

Reaction equation

HRID 1467534 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:19][C:17]3[C:18]4[C:9](=[N:10][NH:11][C:12](=[O:20])[C:13]=4[CH:14]=[CH:15][CH:16]=3)[CH:8]2[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:2]=1>CO.[Pt](=O)=O>[NH:23]1[CH2:24][CH2:25][CH2:26][CH:21]([CH:8]2[C:9]3=[N:10][NH:11][C:12](=[O:20])[C:13]4[CH:14]=[CH:15][CH:16]=[C:17]([C:18]=43)[NH:19][CH:7]2[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:22]1

Participants

4

Reactant 1

HCID 136385312HCID 136385312, compound

Product 1

HCID 136053646HCID 136053646, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 8,9-di(pyridin-3-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (120 mg, 0.35 mmol) and platinum (IV) oxide (60 mg) in methanol (20 mL) was purged in 20 atm hydrogen and stirred at 50° C. for 24 hr. The mixture was filtered and the filtrate was concentrated to give the crude product. The crude product was purified by prep-HPLC to give 9-(piperidin-3-yl)-8-(pyridin-3-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (4 mg, yield: 4%) as a light yellow solid. 1H-NMR (400 MHz, CD3OD) 1.19-1.32 (m, 2H), 1.60-1.65 (m, 2H), 1.94-1.97 (d, J=10.0 Hz, 1H), 2.31-2.43 (m, 2H), 2.82-2.85 (d, J=12.4 Hz, 1H), 3.02-3.05 (d, J=12 Hz, 1H), 3.29-3.32 (dd, J1=2.8 Hz, J2=8.4 Hz, 1H), 4.25-4.26 (d, J=2.8 Hz, 1H), 7.02-7.05 (dd, J1=0.8 Hz, J2=8.8 Hz, 1H), 7.22-7.25 (m, 1H), 7.40-7.53 (m, 3H), 8.25-8.29 (m, 2H); LC-MS (ESI) m/z: 348 (M+1)+.

Workup

  1. customwas purged in 20 atm hydrogen
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give the crude product
  5. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-177a00911afa4c0cb7c19a362a928f1a
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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