HCID 136368568, compound → HCID 136186323, compound

HRID 908040Notes

Reaction equation

HRID 908040 reaction equation
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]1[NH:25][C:23]2[C:24]3[C:15](=[N:16][NH:17][C:18](=[O:26])[C:19]=3[CH:20]=[CH:21][CH:22]=2)[CH:14]1[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[F:33][C:30]1[CH:29]=[CH:28][C:27]([CH:14]2[C:15]3=[N:16][NH:17][C:18](=[O:26])[C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([C:24]=43)[NH:25][CH:13]2[C:9]2[NH:8][CH:12]=[CH:11][N:10]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 1

HCID 136368568HCID 136368568, compound

Product 1

HCID 136186323HCID 136186323, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-(1-benzyl-1H-imidazol-2-yl)-9-(4-fluorophenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (200 mg, 0.46 mmol) and palladium hydroxide (200 mg) in methanol (4 mL) was purged with hydrogen and stirred at 60° C. for 18 hr. Then the mixture was filtered, evaporated to remove the solvent, and washed the solid with ethyl acetate to obtain the title compound (150 mg, yield 94%). LC-MS (ESI) m/z: 348 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 4.93 (d, J=8.4 Hz, 1H), 5.21 (d, J=8.4 Hz, 1H), 7.10 (t, J=8.4 Hz, 2H), 7.21-7.30 (m, 3H), 7.37 (s, 1H), 7.45-7.49 (m, 3H), 4.58 (d, J=10 Hz, 1H), 7.62-7.67 (m, 1H), 7.87 (s, 1H).

Workup

  1. customwas purged with hydrogen
  2. filtrationThen the mixture was filtered
  3. customevaporated
  4. customto remove the solvent
  5. washwashed the solid with ethyl acetate

Sources & evidence

ORD record
ord-aae7692c39114b669ddc00b0ec6740c1
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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