HCID 131729515, compound → HCID 66781521, compound

HRID 1095721Notes

Reaction equation

HRID 1095721 reaction equation
C1C2C(=CC=CC=2)C=CC=1COC([N:15]1[CH2:20][CH2:19][C@H:18]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=2[N:30]=[C:29]([C:32]2[N:36]4[CH:37]=[CH:38][C:39]([O:41][CH2:42][CH2:43][O:44][CH3:45])=[CH:40][C:35]4=[N:34][CH:33]=2)[CH:28]=[CH:27]3)[C@H:17]([OH:46])[CH2:16]1)=O>CCO.[Pd]>[CH3:45][O:44][CH2:43][CH2:42][O:41][C:39]1[CH:38]=[CH:37][N:36]2[C:32]([C:29]3[CH:28]=[CH:27][C:26]4[C:31](=[C:22]([O:21][C@H:18]5[CH2:19][CH2:20][NH:15][CH2:16][C@H:17]5[OH:46])[CH:23]=[CH:24][CH:25]=4)[N:30]=3)=[CH:33][N:34]=[C:35]2[CH:40]=1

Participants

4

Reactant 1

HCID 131729515HCID 131729515, compound

Product 1

HCID 66781521HCID 66781521, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(cis)-Naphthalen-2-ylmethyl-3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (0.030 g, 0.048 mmol) was dissolved in EtOH (1 mL), treated with 10% palladium on carbon (Degussa type, 50 mg), placed under a hydrogen atmosphere (balloon pressure) and stirred for 3 days. The reaction was filtered through a nylon membrane and concentrated in vacuo. The mixture was purified by preparative TLC (10 cm×20 cm×0.5 mm) eluting with 20% (6% NH4OH in MeOH)/ethyl acetate. The recovered product was dissolved in MeOH and treated with 4 M HCl in dioxane then concentrated in vacuo. The residue was re-dissolved in MeOH and re-concentrated three times. The residue was slurried in MeOH (0.3 mL) and added dropwise to Et2O (20 mL). The resultant solid was filtered and dried under N2 to provide the desired product (3 mg). MS ESI (+) m/z 435.1 (M+1) detected.

Workup

  1. filtrationThe reaction was filtered through a nylon membrane
  2. concentrationconcentrated in vacuo
  3. customThe mixture was purified by preparative TLC (10 cm×20 cm×0.5 mm)
  4. washeluting with 20% (6% NH4OH in MeOH)/ethyl acetate
  5. dissolutionThe recovered product was dissolved in MeOH
  6. additiontreated with 4 M HCl in dioxane
  7. concentrationthen concentrated in vacuo
  8. dissolutionThe residue was re-dissolved in MeOH
  9. concentrationre-concentrated three times
  10. additionadded dropwise to Et2O (20 mL)
  11. filtrationThe resultant solid was filtered
  12. customdried under N2

Sources & evidence

ORD record
ord-629b84011d5d428e89dcccedb6103b4c
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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