Sodium Hydroxide → 4-(3-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)-2-fluorobenzoic Acid

HRID 335297Notes

Reaction equation

HRID 335297 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[F:42])[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([F:38])=[C:13]([NH:15][C:16]([C:18]2[N:22]3[CH:23]=[CH:24][C:25]([C:27]4[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[C:29]([F:37])[CH:28]=4)=[CH:26][C:21]3=[N:20][CH:19]=2)=[O:17])[CH:14]=1)=[O:8].[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[F:42])[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([F:38])=[C:13]([NH:15][C:16]([C:18]2[N:22]3[CH:23]=[CH:24][C:25]([C:27]4[CH:36]=[CH:35][C:30]([C:31]([OH:33])=[O:32])=[C:29]([F:37])[CH:28]=4)=[CH:26][C:21]3=[N:20][CH:19]=2)=[O:17])[CH:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71283111Methyl 4-(3-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)-2-fluorobenzoate

Product 1

HCID 712835274-(3-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)-2-fluorobenzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-(3-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)-2-fluorobenzoate (Example 7.1, step 1) (497 mg, 0.862 mmol) and 2M NaOH (4311 μL, 8.62 mmol) in MeOH (2874 μL) was stirred at RT overnight. The solvent was removed in vacuo and the residue was acidified with 2M HCl to pH 2 and extracted with DCM. The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound;

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted with DCM
  3. dry with materialThe organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc95246d06424243be4e6765af724f0c
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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