Ammonium Chloride → HCID 13732596, compound

HRID 1731534Notes

Reaction equation

HRID 1731534 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].Cl[C:13]1[C:18]([C:19](=[O:27])[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[CH:17][N:16]=[C:15]2[N:28]([CH2:31][CH3:32])[N:29]=[CH:30][C:14]=12.[Cl-].[NH4+]>C1COCC1.CCOCC>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([C:18]2[C:13]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])=[C:14]3[CH:30]=[N:29][N:28]([CH2:31][CH3:32])[C:15]3=[N:16][CH:17]=2)=[O:27])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 67180Acetone, oximeHCID 14171315HCID 14171315, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13732596HCID 13732596, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Acetone oxime (1.6 g) was dissolved in 50 ml of THF and potassium t-butoxide (2.46 g) was added. After stirring 30 minutes 6.2 g of 4-chloro-5-(4-chlorobenzoyl)-1-ethyl-1H-pyrazolo[3,4-b]pyridine in 50 ml of THF was added to the solution. After 30 minutes of further stirring, the reaction mixture was distributed between ether and ammonium chloride solution. Drying and evaporation of the organic phase gave a solid which was recrystallized from ethanol to give 4.91 g of product, mp 112°-113° C.

Workup

  1. additionwas added to the solution
  2. customDrying
  3. customevaporation of the organic phase
  4. customgave a solid which
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3267a0f1bc2a437081884f6574a4e360
Source dataset
uspto-grants-1986_11
Patent number
US04622326

Reaction notes

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