Water → HCID 178472229, compound

HRID 869677Notes

Reaction equation

HRID 869677 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.C([CH:20]([C:24](Cl)=[O:25])[C:21](Cl)=[O:22])C.N1[CH:32]=[CH:31]C=CC=1.[OH2:33]>CN(C)C(=O)C.C(O)C>[CH3:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]([NH:17][C:24](=[O:25])[CH2:20][C:21]([O:22][CH2:31][CH3:32])=[O:33])[NH:14][N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 109209242-Ethylpropanedioyl dichlorideHCID 178432134HCID 178432134, compound

Product 1

HCID 178472229HCID 178472229, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-(3-methylquinoxalin-2-yl)-1H-pyrazol-5-amine (5.00 g, 22.2 mmol) in N,N-dimethylacetamide (111 mL) was added ethyl malonyl chloride (5.68 mL, 44.4 mmol) and pyridine (37.2 mL, 45.9 mmol) at 0° C. After being stirred for 3 h, the reaction mixture was diluted with ethanol (118 mL), and stirred at room temperature for 18 h. After adding water (260 mL), the resulting precipitate was collected and washed with water to give ethyl 3-{[3-(3-methylquinoxalin-2-yl)-1H-pyrazol-5-yl]amino}-3-oxopropanoate. MS (APCI): m/z 340 (M+H).

Workup

  1. stirringstirred at room temperature for 18 h
  2. customthe resulting precipitate was collected
  3. washwashed with water

Sources & evidence

ORD record
ord-70778f44a2cc421b819d6571a39f4b51
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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