HCID 136374663, compound → HCID 136344736, compound

HRID 1467517Notes

Reaction equation

HRID 1467517 reaction equation
[CH3:1][N:2]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[C:25]3=[N:26][NH:27][C:28](=[O:33])[C:29]4[CH:30]=[CH:31][CH:32]=[C:23]([C:24]=43)[NH:22][CH:21]2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:16][CH:15]=1)[C:3](=O)OCC1C=CC=CC=1>[Pd].CO>[CH3:1][NH:2][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[C:25]3=[N:26][NH:27][C:28](=[O:33])[C:29]4[CH:30]=[CH:31][CH:32]=[C:23]([C:24]=43)[NH:22][CH:21]2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:18][CH:19]=1.[CH3:3][N:2]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[C:25]3=[N:26][NH:27][C:28](=[O:33])[C:29]4[CH:30]=[CH:31][CH:32]=[C:23]([C:24]=43)[NH:22][CH:21]2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:18][CH:19]=1)[CH3:1]

Participants

5

Reactant 1

HCID 136374663HCID 136374663, compound

Product 2

HCID 136344736HCID 136344736, compoundHCID 136385231HCID 136385231, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl methyl(4-(3-oxo-8-phenyl-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)benzyl)carbamate (80 mg, 0.26 mmol), 10% Pd/C (20 mg) of methanol (50 ml) was stirring at room temperature for 4 h. The mixture solution was then filtered and evaporated under reduced pressure. The residue was purified by prep-HPLC. 3 mg of 9-(4-((methylamino)methyl)phenyl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one and 6 mg of 9-(4-((dimethylamino)methyl)phenyl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one were obtained, yield 9%. For 9-(4-((methylamino)methyl)-phenyl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one: 1H-NMR (400 MHz, CD3OD) δ: 2.50 (s, 3H), 3.87 (s, 2H), 4.38 (d, 1H), 4.75 (d, 1H), 7.15-7.17 (m, 2H), 7.19-7.25 (m, 5H), 7.27-7.28 (m, 3H), 7.57 (d, 1H), 7.65 (t, 1H). LC-MS (ESI) m/z: 383(M+1)+. For 9-(4-((dimethylamino)methyl)phenyl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one: 1H-NMR (400 MHz, CD3OD) δ: 2.31 (s, 6H), 3.57 (s, 2H), 4.33 (d, 1H), 4.73 (d, 1H), 7.10-7.12 (m, 2H), 7.19-7.21 (m, 6H), 7.26-7.27 (m, 2H), 7.58 (d, 1H), 7.64 (t, 1H). LC-MS (ESI) m/z: 397 (M+1)+.

Workup

  1. filtrationThe mixture solution was then filtered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-49fefec404554ad59ba1219d654d9679
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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