Sodium Bicarbonate → HCID 23442320, compound

HRID 2119651Notes

Reaction equation

HRID 2119651 reaction equation
[Cl:1][C:2]1[C:11]2[C:10]([C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH:19]=[N:20][N:21]([CH3:22])[C:3]=12.C(=O)([O-])[OH:24].[Na+]>C(O)(=O)C>[ClH:1].[NH2:16][C:15]1[CH:17]=[CH:18][C:12]([C:10]2[C:11]3[C:2](=[O:24])[C:3]4[N:21]([CH3:22])[N:20]=[CH:19][C:4]=4[NH:5][C:6]=3[CH:7]=[CH:8][CH:9]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23442473HCID 23442473, compound

Product 1

HCID 23442320HCID 23442320, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(9-chloro-1-methyl-1H-pyrazolo[4,3-b]quinolin-8-yl)aniline (EXAMPLE 41, step 2, 41 mg, 0.13 mmol) in 50% aqueous acetic acid (2 ml) was refluxed for 18 h. After cooling to room temperature, saturated sodium hydrogen carbonate (5 ml) was added to the mixture. The formed solid was collected by filtration, washed with water and dried. The obtained solid was dissolved in 10% methanolic hydrochloric acid (3 ml) and the mixture was stirred at room temperature for 18 h. The mixture was concentrated and recrystallized from ethanol to afford 19 mg (46%) of the title compound as a solid.

Workup

  1. temperaturewas refluxed for 18 h
  2. filtrationThe formed solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. dissolutionThe obtained solid was dissolved in 10% methanolic hydrochloric acid (3 ml)
  6. concentrationThe mixture was concentrated
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2c83995046c74905a266dfd141526e22
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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