HCID 86653283, compound → HCID 44156855, compound

HRID 2389274Notes

Reaction equation

HRID 2389274 reaction equation
[O:1]=[C:2]1[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[C:5]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH:25]=[CH2:26])[CH:20]=3)[CH2:15][CH2:14]2)[CH:4]=[C:3]1[C:27]([O:29]CC)=[O:28]>CO.[Pd]>[CH2:25]([C:21]1[CH:20]=[C:19]([N:16]2[CH2:15][CH2:14][N:13]([CH2:12][C:5]3[CH:4]=[C:3]([C:27]([OH:29])=[O:28])[C:2](=[O:1])[N:11]4[C:6]=3[CH:7]=[CH:8][CH:9]=[CH:10]4)[CH2:18][CH2:17]2)[CH:24]=[CH:23][N:22]=1)[CH3:26]

Participants

4

Reactant 1

HCID 86653283HCID 86653283, compound

Product 1

HCID 44156855HCID 44156855, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-oxo-1-{[4-(2-vinylpyridin-4-yl)piperazine-1-yl]methyl}-4H-quinolizine-3-carboxylate (0.050 g, 0.12 mmol) in 3 mL of MeOH under nitrogen was added Pd/C (10 mol %). The reaction was placed under an atmosphere of hydrogen (balloon). After 2 hours, the mixture was filtered and concentrated in vacuo. To a solution of the resulting residue in 1 mL of DMSO was added aqueous lithium hydroxide (0.3 mL). After 2 hours, the reaction mixture was acidified with 6 N HCl to pH ˜2, filtered, and subjected to purification via reverse phase HPLC to provide the title compound which gave a proton NMR consistent with theory and a mass ion (ES+) of 393.1 for M+H+ [C22H24N4O3: 392.45]: 1H NMR (400 MHz, DMSO-d6) δ 9.43 (d, J=7.0 Hz, 1H), 8.56 (s, 1H), 8.51 (d, J=9.0 Hz, 1H), 8.26 (d, J=6.6 Hz, 1H), 8.18 (t, J=7.4 Hz, 1H), 7.16-7.14 (m, 2H), 4.67-3.17 (m, 10H), 2.76 (q, J=7.5 Hz, 2H), 1.26 (q, J=7.5 Hz, 1H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. additionTo a solution of the resulting residue in 1 mL of DMSO was added aqueous lithium hydroxide (0.3 mL)
  4. waitAfter 2 hours
  5. filtrationfiltered
  6. customsubjected to purification via reverse phase HPLC

Sources & evidence

ORD record
ord-fc53e12d8f23485aabc2da6fdbec9757
Source dataset
uspto-grants-2012_09
Patent number
US08273737B2

Reaction notes

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