Acetic Acid → HCID 178432132, compound

HRID 869709Notes

Reaction equation

HRID 869709 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]([NH2:17])[NH:14][N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:18]1([C:21](=O)[CH2:22][C:23](OCC)=[O:24])[CH2:20][CH2:19]1.C[O-].[Na+].C(O)(=O)C>COCCO.O>[CH:18]1([C:21]2[CH:22]=[C:23]([OH:24])[N:14]3[N:13]=[C:12]([C:3]4[C:2]([CH3:1])=[N:11][C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[N:4]=4)[CH:16]=[C:15]3[N:17]=2)[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 10942334Sodium MethoxideHCID 178432134HCID 178432134, compound

Product 1

HCID 178432132HCID 178432132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 3-(3-methylquinoxalin-2-yl)-1H-pyrazol-5-amine (Example 1.001 (c)) (200 mg, 0.888 mmol), ethyl 3-cyclopropyl-3-oxopropanoate (416 mg, 2.66 mmol), and sodium methoxide (28% in methanol, 1.03 g, 5.34 mmol) in 2-methoxyethanol (2.0 mL) was refluxed for 10 h. After being cooled to ambient temperature, the reaction mixture was acidified to pH 3-4 with acetic acid. The mixture was diluted with water and the resulting precipitate was collected and washed with diisopropyl ether to give 5-cyclopropyl-2-(3-methylquinoxalin-2-yl)pyrazolo[1,5-a]pyrimidin-7-ol. MS (APCI): m/z 318 (M+H).

Workup

  1. temperaturewas refluxed for 10 h
  2. customthe resulting precipitate was collected
  3. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-010a75a984ea4916aefec5a4827670c9
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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