Monoethyl malonate → HCID 178472229, compound

HRID 869678Notes

Reaction equation

HRID 869678 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:18]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:19][C:20](O)=[O:21].Cl.C(N=C=NCCCN(C)C)C>N1C=CC=CC=1>[CH3:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]([NH:17][C:20](=[O:21])[CH2:19][C:18]([O:24][CH2:25][CH3:26])=[O:23])[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

5

Reactant 3

HCID 70615Monoethyl malonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178432134HCID 178432134, compound

Product 1

HCID 178472229HCID 178472229, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 3-(3-methylquinoxalin-2-yl)-1H-pyrazol-5-amine (5.00 g, 22.2 mmol) and ethyl hydrogen malonate (2.88 mL, 24.4 mmol) in pyridine (89 mL) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.38 g, 33.3 mmol) at 0° C. and stirred for 30 min. The reaction mixture was stirred for 1 h at room temperature and then concentrated in vacuo. The residue was diluted with water (100 mL) and the resulting precipitate was collected and washed with water followed by diethyl ether 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. stirringThe reaction mixture was stirred for 1 h at room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water (100 mL)
  4. customthe resulting precipitate was collected
  5. washwashed with water

Sources & evidence

ORD record
ord-2e2c0ee51eb242b281db077cf2d12210
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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