Dimethyl Sulfoxide → HCID 67586737, compound

HRID 1458753Notes

Reaction equation

HRID 1458753 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].CS(C)=O.[NH2:21][CH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1.CS(O)(=O)=O>CO.O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:21][CH:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH2:24][CH2:23]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6395Methanesulfonic AcidHCID 123445(+-)-1-AminoindanHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 67586737HCID 67586737, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 0.0043 mol), DMSO (3 ml) and 1-aminoindane (1 g) is heated at 110° C. for 16 hours. The reaction mixture is cooled, and then is poured into water (100 ml). The solid that forms is collected by filtration and dried to afford the product as the free base. The free base is dissolved in methanol and then is treated with methanesulfonic acid. The methanol is evaporated, and the residue is crystallized from hot methanol/2-propanol and then is recrystallized from hot methanol/2-propanol to afford 717 mg of 1-ethyl-N-(1-indanyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.CH3SO3H, m.p. 233°-235° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe solid that forms is collected by filtration
  3. customdried
  4. customto afford the product as the free base
  5. customThe methanol is evaporated
  6. customthe residue is crystallized from hot methanol/2-propanol
  7. customis recrystallized from hot methanol/2-propanol

Sources & evidence

ORD record
ord-3a76cf3e791a4cd8913766dce52c4268
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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