Sodium Hydroxide → HCID 178522091, compound

HRID 1820915Notes

Reaction equation

HRID 1820915 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:32]=[CH:31][CH:30]=[CH:29][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([O:27]C)=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1.[OH-].[Na+]>O1CCCC1CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:32]=[CH:31][CH:30]=[CH:29][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501152HCID 178501152, compound

Product 1

HCID 178522091HCID 178522091, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

Methyl trans-4-{[(2-{[(5-chloropyridin-2-yl)-amino]carbonyl}benzofuran-3-yl)amino]carbonyl}cyclohexane-carboxylate (300 mg) obtained in Example 8(1) is suspended in tetrahydrofuran-methanol (4:1) (10 ml) and thereto is added 10% aqueous sodium hydroxide solution (1 ml). The mixture is warmed to room temperature and stirred for 17 hours. The reaction solution is concentrated under reduced pressure, thereto added ice-water, and the mixture is acidified by addition of 10% hydrochloric acid. The precipitates are collected by filtration, washed with water, and dried to give trans-4-{[(2-{[(5-chloropyridin-2-yl)amino]carbonyl}benzofuran-3-yl)amino]carbonyl}-cyclohexanecarboxylic acid (270 mg).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionadded ice-water, and the mixture is acidified by addition of 10% hydrochloric acid
  3. filtrationThe precipitates are collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-21f273a96d664838a0e7b6b226fe7795
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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