Methanesulfonic Acid → HCID 86750597, compound

HRID 1458756Notes

Reaction equation

HRID 1458756 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) is stirred at room temperature overnight. The reaction mixture is poured into water and then is basified with NaOH. The layers are separated, and then the aqueous layer is acidified with acetic acid. The precipitate that forms is collected by filtration, washed with water and dried to afford the product as the free base. The free base is taken up in methanol and treated with methanesulfonic acid. The methanol is evaporated and the solid residue is 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 are separated
  2. filtrationThe precipitate that forms is collected by filtration
  3. washwashed with water
  4. customdried
  5. customto afford the product as the free base
  6. customThe methanol is evaporated
  7. customthe solid residue is recrystallized from 2-propanel/methanol/ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-03dfa62b3a9c46afbc2c2cff8a8b2811
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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