Hydrochloric Acid → 3,5-difluoro-4-(((2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)methyl)benzoic acid

HRID 929927Notes

Reaction equation

HRID 929927 reaction equation
[OH-:1].[Na+].C([C:5]1[CH:31]=[C:30]([F:32])[C:8]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:19]=[N:20][N:21]([CH2:23]C(NC(C)C)=O)[CH:22]=3)[N:12]=2)=[C:7]([F:33])[CH:6]=1)#N.Cl.C1[CH2:39][O:38]CC1.CO>>[F:32][C:30]1[CH:31]=[C:5]([CH:6]=[C:7]([F:33])[C:8]=1[CH2:9][NH:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]2[CH:19]=[N:20][N:21]([CH3:23])[CH:22]=2)[N:12]=1)[C:39]([OH:38])=[O:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 727064692-(4-((4-((4-cyano-2,6-difluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)-N-isopropylacetamide

Product 1

HCID 900238453,5-difluoro-4-(((2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)methyl)benzoic acid

Procedure

2M NaOH(aq) (2 mL, 4 mmol) was added to a stirred mixture of methyl 3,5-difluoro-4-(((2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)methyl)benzoate (370 mg, 1 mmol, prepared by Procedure A) in 3:1 v/v THF/MeOH (40 mL) and the reaction was stirred at room temperature overnight. The mixture was neutralized with 1M hydrochloric acid and concentrated in vacuo to afford 3,5-difluoro-4-(((2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)methyl)benzoic acid (theoretically 360 mg) which was used in the next step without purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f54b5b653ab34f849b4288fd686ad603
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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