Sodium Hydroxide → HCID 135428026, compound

HRID 2377850Notes

Reaction equation

HRID 2377850 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]1[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][C:12](=[O:28])[C:11]=1[C:29]1[NH:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[N:30]=1)[CH2:2]2.[OH-].[Na+]>Br.CC(O)=O>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@H:3]([NH:9][C:10]1[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][C:12](=[O:28])[C:11]=1[C:29]1[NH:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136348999HCID 136348999, compound

Product 1

HCID 135428026HCID 135428026, compound

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Conditions

Temperature
60 °C

Procedure

4-[(3S)-1-azabicyclo[2.2.2]oct-3-ylamino]-3-(1H-benzimidazol-2-yl)-6-(4methoxyphenyl)quinolin-2(1H)-one (Example 70) was dissolved in 30% HBr/AcOH and heated at 60° C. until the reaction was complete. The resulting mixture was allowed to cool, and it was then neutralized with 2 M NaOH. The resulting mixture was extracted with EtOAc, and the organic layers were dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by reverse phase HPLC to give the desired product. MS m/z 478.6 (M+H).

Workup

  1. temperatureto cool
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-966a97700b284025af44ac29fe897f27
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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