9-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one → HCID 178430837, compound

HRID 1467590Notes

Reaction equation

HRID 1467590 reaction equation
C([N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]1[CH:14]1[C:19]2=[N:20][NH:21][C:22](=[O:27])[C:23]3[CH:24]=[CH:25][CH:26]=[C:17]([C:18]=32)[NH:16][CH:15]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH3:13][C:11]1[N:10]=[C:9]([CH:14]2[C:19]3=[N:20][NH:21][C:22](=[O:27])[C:23]4[CH:24]=[CH:25][CH:26]=[C:17]([C:18]=43)[NH:16][CH:15]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[NH:8][CH:12]=1

Participants

4

Reactant 1

HCID 1363747039-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

Product 1

HCID 178430837HCID 178430837, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 9-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (40 mg, 0.09 mmol) and palladium hydroxide on carbon catalyst (40 mg, 20% wt) in anhydrous methanol (15 mL) was purged with hydrogen (1 bar) at room temperature for 12 hr. The mixture was filtered and the filtrate was concentrated to give crude product, which was purified by pre-HPLC to give 9-(4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (27 mg, yield 87%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 2.22 (dd, 3H), 4.77-4.86 (m, 2H), 7.06 (s, 1H), 7.20 (d, 1H), 7.36 (t, 5H), 7.55 (d, 1H), 7.62 (t, 1H); LC-MS (ESI) m/z: 3-(4 (M+1)+.

Workup

  1. customwas purged with hydrogen (1 bar) at room temperature for 12 hr
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give crude product, which
  5. customwas purified by pre-HPLC

Sources & evidence

ORD record
ord-0b6eb826dac742b09065f2439e779a47
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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