Monoethyl malonate → HCID 178472230, compound

HRID 869689Notes

Reaction equation

HRID 869689 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([CH3:18])[C:8]([C:12]3[CH:16]=[C:15]([NH2:17])[NH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:19]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:20][C:21](O)=[O:22].Cl.C(N=C=NCCCN(C)C)C>N1C=CC=CC=1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([CH3:18])[C:8]([C:12]3[CH:16]=[C:15]([NH:17][C:21](=[O:22])[CH2:20][C:19]([O:25][CH2:26][CH3:27])=[O:24])[NH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70615Monoethyl malonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178432188HCID 178432188, compound

Product 1

HCID 178472230HCID 178472230, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 3-(7-fluoro-3-methylquinoxalin-2-yl)-1H-pyrazol-5-amine (45.7 g, 188 mmol) in pyridine (750 mL) was added ethyl hydrogen malonate (5.35 mL, 62.5 mmol) and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (54.0 g, 282 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 3 h, and then concentrated in vacuo. The residue was triturated with water, ethanol and acetone subsequently to give ethyl 3-{[3-(7-fluoro-3-methylquinoxalin-2-yl)-1H-pyrazol-5-yl]amino}-3-oxopropanoate. MS (APCI): m/z 358 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with water, ethanol and acetone subsequently

Sources & evidence

ORD record
ord-9e549b48b3dc4880b648b7bcd3b23663
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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