HCID 136090367, compound → HCID 136090407, compound

HRID 131462Notes

Reaction equation

HRID 131462 reaction equation
[CH2:1]([O:4][CH2:5][C@@H:6]1[N:11]([CH3:12])[CH2:10][CH2:9][N:8]([C:13]2[C:22]3[CH:21]=[C:20]([CH3:23])[S:19][C:18]=3[NH:17][C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)[CH2:7]1)[CH:2]=[CH2:3]>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:12][N:11]1[CH2:10][CH2:9][N:8]([C:13]2[C:22]3[CH:21]=[C:20]([CH3:23])[S:19][C:18]=3[NH:17][C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)[CH2:7][C@@H:6]1[CH2:5][O:4][CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 136090367HCID 136090367, compound

Product 1

HCID 136090407HCID 136090407, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Stir (R)-10-(3-allyloxymethyl-4-methyl-piperazin-1-yl)-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (270 mg), 20% palladium hydroxide (Degaussa type, 15 mg) in ethanol (0.014M)) under hydrogen atmosphere (1 atm) for 4 hours at room temperature. Filter and evaporate the solvent to afford the title compound as a yellow solid (268 mg): 1H NMR (CDCl3) δ 0.90 (t, 3H), 1.58 (m, 2H), 2.30 (s, 3H), 2.33 (m, 2H), 2.39 (s, 3H), 2.84 (m, 2H), 3.14 (t, 1H), 3.38 (t, 2H), 3.49 (d, 1H), 3.58 (d, 1H), 3.95 (d, 1H), 4.07 (d, 1H), 4.94 (s, 1H), 6.31 (s, 1H), 6.60 (d, 1H), 6.85 (t, 1H), 6.95 (t, 1H), 7.02 (d, 1H); MS (ESI) m/z (rel intensity) 385 (100).

Workup

  1. filtrationFilter
  2. customevaporate the solvent

Sources & evidence

ORD record
ord-6e0ccf2b342e4947a5c95f5b1361b281
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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