Hydrochloric Acid → HCID 86600318, compound

HRID 1866087Notes

Reaction equation

HRID 1866087 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=2[Cl:16])=[C:6]([NH:17][C@@H:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])[N:5]2[N:23]=[CH:24][C:25]([C:26]([O:28]C)=[O:27])=[C:4]2[N:3]=1.[OH-].[K+].O.Cl>O1CCOCC1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=2[Cl:16])=[C:6]([NH:17][C@@H:18]([CH:20]([CH3:21])[CH3:22])[CH3:19])[N:5]2[N:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[C:4]2[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 86600316HCID 86600316, compound

Product 1

HCID 86600318HCID 86600318, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.35 g (0.001 mol) of atropisomer A of methyl 5-chloro-6-(2-chloro-4-cyanophenyl)-7-[(R)-3-methyl-2-butylamino]pyrazolo[1,5-a]pyrimidine-3-carboxylate were dissolved in 4.6 ml of dioxane. 0.37 g (0.009 mol) of potassium hydroxide in 4.6 ml of aqueous solution was added at room temperature, and the reaction mixture was then stirred for 12 hours. The mixture was then poured into water and acidified with hydrochloric acid. 0.15 g of product was filtered off. The product was chromatographed on silica gel using ethyl acetate:cyclohexane:acetic acid=40:10:1, which gave the atropisomer A of 5-chloro-6-(2-chloro-4-cyanophenyl)-7-[(R)-3-methyl-2-butyl-amino]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid.

Workup

  1. filtration0.15 g of product was filtered off
  2. customThe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-d741f387826f4d009f681da23bcbefc0
Source dataset
uspto-grants-2009_12
Patent number
US07629294B2

Reaction notes

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