Sodium Hydroxide → HCID 71283788, compound

HRID 335293Notes

Reaction equation

HRID 335293 reaction equation
[CH3:1][C:2]1([CH3:42])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([F:41])=[C:16]([NH:18][C:19]([C:21]2[N:25]3[CH:26]=[CH:27][C:28]([C:30]4[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[C:32]([F:40])[CH:31]=4)=[CH:29][C:24]3=[N:23][CH:22]=2)=[O:20])[CH:17]=1)=[O:11].[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:42])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([F:41])=[C:16]([NH:18][C:19]([C:21]2[N:25]3[CH:26]=[CH:27][C:28]([C:30]4[CH:39]=[CH:38][C:33]([C:34]([OH:36])=[O:35])=[C:32]([F:40])[CH:31]=4)=[CH:29][C:24]3=[N:23][CH:22]=2)=[O:20])[CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71283568HCID 71283568, compound

Product 1

HCID 71283788HCID 71283788, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture comprising methyl 4-(3-(5-(2-(2,2-dimethylpyrrolidin-1-yl)ethylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)-2-fluorobenzoate (step 2) (409 mg, 0.711 mmol) and sodium hydroxide (142 mg, 3.55 mmol) in MeOH (5 ml) was heated at 60° C. overnight. The reaction mixture was concentrated under vacuum and the resulting residue was dissolved in water and adjusted to pH 5 using 1M HCl. The solid precipitate was collected by filtration and dried at 45° C. The aqueous portion was concentrated in vacuo and the residue was sonicated in 5% MeOH in DCM. The resulting suspension was filtered and the filtrate was combined with the solid precipitate from the first filtration. The combined product were evaporated to dryness and dried at 45° C. in the vacuum oven.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe resulting residue was dissolved in water
  3. filtrationThe solid precipitate was collected by filtration
  4. customdried at 45° C
  5. concentrationThe aqueous portion was concentrated in vacuo
  6. customthe residue was sonicated in 5% MeOH in DCM
  7. filtrationThe resulting suspension was filtered
  8. filtrationthe filtrate was combined with the solid precipitate from the first filtration
  9. customThe combined product were evaporated to dryness
  10. customdried at 45° C. in the vacuum oven

Sources & evidence

ORD record
ord-12e91d5042c547ee914356c50c58697d
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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