Ethanol → HCID 86744251, compound

HRID 1087786Notes

Reaction equation

HRID 1087786 reaction equation
Cl[CH:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.[CH3:23][CH:24]([CH3:33])[C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].[Na].C(O)C>C(Cl)Cl>[Cl:22][C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([N:3]3[CH:2]([CH:26]([C:25](=[O:32])[CH:24]([CH3:33])[CH3:23])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:10]4[C:5](=[N:6][CH:7]=[CH:8][N:9]=4)[C:4]3=[O:11])=[N:13]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 81583Ethyl isobutyrylacetateHCID 5360545SodiumHCID 19900415HCID 19900415, compound

Product 1

HCID 86744251HCID 86744251, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-{6-(7-chloro-1,8-naphthyridin-2-yl)-6, 7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl}-4-methyl-3oxopentanoate may be obtained as in Example 29, but starting with 5-chloro-6-(7-chloro-1,8-naphthyridin-2-yl)-6, 7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazine (13 g), ethyl 4-methyl-3-oxopentanoate (8.7 g), sodium (1.1 g), ethanol (400 cc) and methylene chloride (200 cc). After recrystallization in methanol, ethyl 2-{6-(7-chloro-1, 8-naphthyridin-2-yl)-6,7-dihydro-7-oxo-5H-pyrrolo[3, 4-b]pyrazin-5yl}-4-methyl-3-oxopentanoate (7.8 g), m.p. 214° C., is thereby obtained.

Workup

  1. customAfter recrystallization in methanol

Sources & evidence

ORD record
ord-2a16b2bd09914378bce59d87dbdfa6a9
Source dataset
uspto-grants-1990_10
Patent number
US04960779

Reaction notes

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