1-methyl-1H-pyrazol-4-amine → HCID 178481769, compound

HRID 2119666Notes

Reaction equation

HRID 2119666 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.[Cl:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][CH:14]2[CH2:19][CH:18]([C:20](OCC)=[O:21])[C:17](=O)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH:14]2[CH2:15][CH2:16][C:17]3[N:7]=[C:5]4[CH:4]=[N:3][N:2]([CH3:1])[C:6]4=[C:20]([OH:21])[C:18]=3[CH2:19]2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 47709901-methyl-1H-pyrazol-4-amineHCID 23442304HCID 23442304, compound

Product 1

HCID 178481769HCID 178481769, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1-methyl-1H-pyrazol-4-amine ((J. Catalan et al., J. Heterocycl. Chem., 1985, 22, 997), 200 mg, 2.06 mmol), ethyl 5-(4-chlorobenzyl)-2-oxocyclohexanecarboxylate (EXAMPLE 69, step 3, 1.43 g, 4.85 mmol), and p-toluenesulfonic acid monohydrate (10 mg, 0.05 mmol) in toluene (15 ml) was stirred at 120° C. for 2.5 h. After cooling to room temperature, the solvent was removed in vacuo. The residue (ca. 1.5 g) was dissolved in diphenyl ether (10 ml) and heated at 240° C. for 1 h. After cooling to room temperature, the formed solid was collected by filtration, and washed with diisopropyl ether to give 231 mg (34%) of 7-(4-chlorobenzyl)-1-methyl-5,6,7,8-tetrahydro-1H-pyrazolo[4,3-b]quinolin-9-ol. 105 mg of this compound was treated with methanolic hydrochloric acid (5 ml) and the mixture was evaporated. The obtained solid was recrystallized from methanol/diisopropyl ether to give 100 mg of the title compound as a gray crystal.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue (ca. 1.5 g) was dissolved in diphenyl ether (10 ml)
  3. temperatureheated at 240° C. for 1 h
  4. temperatureAfter cooling to room temperature
  5. filtrationthe formed solid was collected by filtration
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-e894ebd8008d4025a920c8702ec4602b
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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