Hydrochloric Acid → HCID 178524191, compound

HRID 16680Notes

Reaction equation

HRID 16680 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-9e283a4f0bbc4b478b927290b453ba91
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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