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Sodium Hydroxide → HCID 178484566, compound

HRID 1820912
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Reaction equation

HRID 1820912 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:33]=[CH:32][C:31]([C:34]([O:36]C)=[O:35])=[CH:30][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1.[OH-].[Na+]>O1CCCC1CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:33]=[CH:32][C:31]([C:34]([OH:36])=[O:35])=[CH:30][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178497414HCID 178497414, compound

Product 1

HCID 178484566HCID 178484566, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

Methyl 2-{[(5-chloropyridin-2-yl)amino]carbonyl}-3-[({trans-4-[(dimethylamino)carbonyl]cyclohexyl}carbonyl)-amino]benzofuran-5-carboxylate (1.35 g) obtained in Example 1 is suspended in tetrahydrofuran-methanol (4:1) (20 ml). After adding a solution of sodium hydroxide (205 mg) in water (5 ml), the mixture is warmed to room temperature and stirred for 18 hours. The reaction solution is concentrated under reduced pressure, thereto poured 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 the title compound (1.23 g).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionpoured 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-0f62334966114bc1a11d3fa2a1109086
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07605158B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes