Hydrochloric Acid → 4-({2-[(5-Cyanopyridin-2-yl)amino]ethyl}amino)-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrazine-2-carboxylic acid hydrochloride

HRID 444857Notes

Reaction equation

HRID 444857 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH2:11][NH:12][C:13]2[C:14]3[N:15]([N:27]=[C:28]([C:30]([O:32]CC)=[O:31])[CH:29]=3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[N:18]=2)=[N:7][CH:8]=1)#[N:2].O.[OH-].[Na+].Cl>COCCOC>[ClH:25].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH2:11][NH:12][C:13]2[C:14]3[N:15]([N:27]=[C:28]([C:30]([OH:32])=[O:31])[CH:29]=3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[N:18]=2)=[N:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 25168329Ethyl 4-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrazine-2-carboxylate

Product 1

HCID 670603404-({2-[(5-Cyanopyridin-2-yl)amino]ethyl}amino)-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrazine-2-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

80 mg (0.16 mmol) of ester (Example 3) were dissolved in 5 ml of 1,2-dimethoxyethane, and 2.5 ml of water and 0.43 ml (0.4 mmol) of 1N sodium hydroxide solution were added. The solution was stirred at RT for 2 h. 20 ml of dilute hydrochloric acid (pH 3) were initially charged, and the reaction solution was slowly added dropwise. The mixture was stirred for another 30 min, and the product was filtered off and washed with diethyl ether. This gave, after drying under high vacuum, 70 mg (84% of theory) of the product as a solid.

Workup

  1. additionthe reaction solution was slowly added dropwise
  2. stirringThe mixture was stirred for another 30 min
  3. filtrationthe product was filtered off
  4. washwashed with diethyl ether
  5. dry with materialThis gave, after drying under high vacuum, 70 mg (84% of theory) of the product as a solid

Sources & evidence

ORD record
ord-ad6dc08c47034b0ca0011ba17bb95ba9
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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