Diethyl Malonate → HCID 57298849, compound

HRID 1197804Notes

Reaction equation

HRID 1197804 reaction equation
ClC1C(C(C)CC)=NC(C2C=NC=CC=2)=CN=1.[NH:18]([C:20]1[C:25]([CH:26]([CH3:29])[CH2:27][CH3:28])=[N:24][C:23]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:22][N:21]=1)[NH2:19].[C:36](OCC)(=O)[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>C(O)C.O>[CH3:29][CH:26]([C:25]1[C:20]2[N:21]([C:36]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[N:19][N:18]=2)[CH:22]=[C:23]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[N:24]=1)[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 19104896HCID 19104896, compoundHCID 19104976HCID 19104976, compound

Product 1

HCID 57298849HCID 57298849, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

In a manner analogous to Example 1, by condensing 3-(2-amino-1,1-diethoxyethyl)pyridine with 3-methyl-2-oxopentanoic acid there is obtained rac-N-[2,2-diethoxy-2-(3-pyridyl)ethyl]-3-methyl-2-oxovaleramide as an amorphous, colorless solid. Subsequent acidic hydrolysis to rac-3-methyl-2-oxo-N-[(3-pyridylcarbonyl)methyl]valeramide hydrochloride (beige, crystalline solid, melting point 158°-159°) and ring closure gives rac-3-(1-methylpropyl)-5-(3-pyridyl)-2(1H)-pyrazinone as a yellow solid, melting point 146°-148° (from acetonitrile). The conversion into rac-2-chloro-3-(1-methylpropyl)-5-(3-pyridyl)pyrazine is also effected analogously to Example 1. Hydrazinolysis to rac-2-hydrazino-3-(1-methylpropyl)-5-(3-pyridyl)pyrazine in the form of beige crystals, melting point 166°-167° (from ethanol/water) and subsequent condensation with diethyl malonate gives ethyl rac-8-(1-methylpropyl)-6-(3-pyridyl)-s-triazolo[4,3-a]pyrazine-3-acetate, MS: 335 (M)+, which is converted by saponification into the above acid, MS: 267 (M-CO 2)+.

Sources & evidence

ORD record
ord-1e5ae8250435452fb06093661c1e9622
Source dataset
uspto-grants-1994_01
Patent number
US05278161

Reaction notes

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