HCID 136385312, compound → HCID 136053646, compound

HRID 1967914Notes

Reaction equation

HRID 1967914 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) δ 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-d1f08aac5a9f49258750a8e73f11859d
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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