Methanesulfonic Acid → HCID 86750597, compound

HRID 977148Notes

Reaction equation

HRID 977148 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:26]C)=[CH:11][CH:10]=3)[CH3:2].B(Br)(Br)Br.[OH-].[Na+].CS(O)(=O)=O>CO.O.C(Cl)CCl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][C:18]4[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([OH:26])=[CH:11][CH:10]=3)[CH3:2]

Participants

8

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 19592238HCID 19592238, compound

Product 1

HCID 86750597HCID 86750597, compoundYield 37.9%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-6-methoxy-N-(4-methoxyphenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (1.0 g, 2.76 mmol), boron tribromide (6 mL, 6 mmol) and 1,2-ethylenedichloride (30 mL) was stirred at room temperature overnight. The reaction mixture was poured into water and then was basified with NaOH. The layers were separated and then the aqueous layer was acidified with acetic acid. The precipitate which formed was collected by filtration, washed with water and dried to afford the product as the free base. The free base was taken up in methanol and treated with methanesulfonic acid. The methanol was evaporated and the solid residue was recrystallized from 2-propanel/methanol/ether and dried in vacuo to afford 350 mg of 1-ethyl-6-hydroxy-N-(4-hydroxyphenyl methyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.CH3SO3H.

Workup

  1. customThe layers were separated
  2. customThe precipitate which formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried
  6. customto afford the product as the free base
  7. customThe methanol was evaporated
  8. customthe solid residue was recrystallized from 2-propanel/methanol/ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-ba58e4fd51ab477caf314d0b90b36ff7
Source dataset
uspto-grants-1997_03
Patent number
US05614530

Reaction notes

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