Citric Acid → HCID 71612269, compound

HRID 1774547Notes

Reaction equation

HRID 1774547 reaction equation
[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:15]([F:16])=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[CH:12][C:11]=3[F:20])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][C:29]=4[C:34]([O:36]CC)=[O:35])[C:24]([O:39][CH3:40])=[CH:23][N:22]=3)[C:5]=2[CH3:41])[CH2:3][CH2:2]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:11]([F:20])=[CH:12][C:13]([O:17][CH2:18][CH3:19])=[CH:14][C:15]=3[F:16])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[C:29]([C:34]([OH:36])=[O:35])=[CH:30][N:31]=[CH:32][CH:33]=4)[C:24]([O:39][CH3:40])=[CH:23][N:22]=3)[C:5]=2[CH3:41])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 71612022HCID 71612022, compound

Product 1

HCID 71612269HCID 71612269, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 722 mg of ethyl 4-({2-[5-cyclopropyl-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazol-3-yl]-5-methoxypyrimidin-4-yl}amino)-pyridine-3-carboxylate 2-6-5 (1.28 mmol, 1.0 eq) in 13 mL THF and 1.6 mL methanol were added 256 mg sodium hydroxide (6.39 mmol, 5.0 eq). The mixture was stirred for 45 minutes at rt. Using 10% aqueous citric acid the pH of the mixture was adjusted to 3.5. The resulting suspension was filtered. The precipitate was washed with water and ethanol and subsequently dried to provide 660 mg of the desired product (1.11 mmol, 87%) as 90% pure target compound.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washThe precipitate was washed with water and ethanol
  3. customsubsequently dried

Sources & evidence

ORD record
ord-e10032e9722d43cd89dde6c55694f53e
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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