Sodium Hydroxide → HCID 67147812, compound

HRID 2426899Notes

Reaction equation

HRID 2426899 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:19]1([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][N:30]=[C:29]3[N:33](S(C4C=CC(C)=CC=4)(=O)=O)[C:34]([C:36]4[C:44]5[C:39](=[CH:40][C:41]([O:47][CH3:48])=[C:42]([O:45][CH3:46])[CH:43]=5)[N:38]([CH3:49])[CH:37]=4)=[CH:35][C:28]=23)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>O1CCCC1.O>[CH:19]1([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][N:30]=[C:29]3[NH:33][C:34]([C:36]4[C:44]5[C:39](=[CH:40][C:41]([O:47][CH3:48])=[C:42]([O:45][CH3:46])[CH:43]=5)[N:38]([CH3:49])[CH:37]=4)=[CH:35][C:28]=23)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 67147757HCID 67147757, compound

Product 1

HCID 67147812HCID 67147812, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1 cm3 of a 1M solution of tetrabutylammonium fluoride (TBAF) in tetrahydrofuran is added, at a temperature in the region of 20° C., to a solution of 0.14 g of cyclohexyl [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine in 10 cm3 of tetrahydrofuran. The reaction medium is stirred at this same temperature for 15 hours, and then refluxed for 24 hours. After cooling, the reaction medium is evaporated to dryness under reduced pressure. 4 cm3 of water are added. The solid formed is filtered off on a sinter funnel, and washed with water and then with ethyl ether. The solid obtained is taken up in water and the medium is basified to pH 10 with 0.1N sodium hydroxide. The product is extracted five times with dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.029 g of cyclohexyl [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine is thus obtained, the characteristics of which are as follows:

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureAfter cooling
  3. customthe reaction medium is evaporated to dryness under reduced pressure
  4. addition4 cm3 of water are added
  5. customThe solid formed
  6. filtrationis filtered off on a sinter funnel
  7. washwashed with water
  8. customThe solid obtained
  9. extractionThe product is extracted five times with dichloromethane
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b47ef7a480d496885cb12121461162d
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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