HCID 135924347, compound → HCID 136385171, compound

HRID 1467535Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([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:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:3][CH:2]=1>[Pt](=O)=O>[NH:24]1[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:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 8,9-di(pyridin-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (120 mg, 0.35 mmol), platinum (IV) oxide (60 mg) and concentrate hydrochloric acid (0.3 mL) in methanol (20 mL) was stirred at 50° C. under 20 atm of hydrogen. The mixture was filtered out and the filtrate was concentrated to give crude product. The crude product was purified by prep-HPLC to give 9-(piperidin-4-yl)-8-(pyridin-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7 H)-one (17.6 mg, yield: 16%) as a light yellow solid. 1H-NMR (400 MHz, CD3OD) 1.25-1.39 (m, 1H), 1.40-1.52 (m, 1H), 1.60-1.70 (m, 1H), 1.75-1.84 (m, 1 H), 1.89-1.98 (m, 1H), 2.50-2.57 (m, 1H), 2.60-2.66 (m, 1H), 3.09-3.21 (m, 2H), 3.34-3.37 (dd, J1=8 Hz, J2=2.4 Hz, 1H), 4.24 (d, J=2 Hz, 1H), 7.02-7.04 (dd, J1=8 Hz, J2=0.8 Hz, 1H), 7.09-7.11 (dd, J1=4.8 Hz, J2=1.2 Hz, 2H), 7.41-7.43 (dd, J1=7.6 Hz, J2=0.8 Hz, 1H), 7.50-7.54 (t, J=8 Hz, 1H), 8.30-8.32 (dd, J1=4.4 Hz, J2=1.6 Hz, 2H); LC-MS (ESI) m/z: 348 (M+1)+.

Workup

concentrationconcentrate hydrochloric acid (0.3 mL) in methanol (20 mL)
filtrationThe mixture was filtered out
concentrationthe filtrate was concentrated
customto give crude product
customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-c0e78e606d7541d8915869156bf97626
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999987B2

Reaction notes

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