Hydrochloric Acid → HCID 178524191, compound

HRID 2109028Notes

Reaction equation

HRID 2109028 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([C:20]([O:22]C)=[O:21])=[CH:16][CH:17]=3)[C:12]=2[NH:24][C:25]([C@H:27]2[CH2:32][CH2:31][C@H:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C:34]3=[O:39])[CH2:29][CH2:28]2)=[O:26])=[O:10])=[N:6][CH:7]=1.[OH-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([C:20]([OH:22])=[O:21])=[CH:16][CH:17]=3)[C:12]=2[NH:24][C:25]([C@H:27]2[CH2:28][CH2:29][C@H:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C:34]3=[O:39])[CH2:31][CH2:32]2)=[O:26])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178497416HCID 178497416, compound

Product 1

HCID 178524191HCID 178524191, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylate (9.40 g) obtained in Example 39 is suspended in tetrahydrofuran (135 ml), and thereto is added 1 N aqueous sodium hydroxide solution (34 ml) under ice-cooling. The mixture is warmed to room temperature, and stirred for 3 hours. To the reaction solution is poured 2N hydrochloric acid (17 ml) under ice-cooling, and the reaction solution is concentrated under reduced pressure. The residue is suspended in water and the precipitates are collected by filtration. The resulting solid is washed with water and diethyl ether to give the title compound (7.83 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationthe reaction solution is concentrated under reduced pressure
  4. filtrationthe precipitates are collected by filtration
  5. washThe resulting solid is washed with water and diethyl ether

Sources & evidence

ORD record
ord-d1a5e31769c544a9baa9069173e24503
Source dataset
uspto-grants-2009_04
Patent number
US07514449B2

Reaction notes

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