Lithium diisopropylamide → HCID 12074627, compound

HRID 478752Notes

Reaction equation

HRID 478752 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH:13]=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](OC)=[O:32])=[CH:21][CH:20]=1.[Li+].CC([N-]C(C)C)C>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:11]3[C:12](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:30]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:22]3[CH:21]=[CH:20][N:19]=[CH:24][CH:23]=3)[C:31]2=[O:32])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 121149522-(3-Nitro-phenylamino)-pyridine-3-carbaldehydeHCID 18002613HCID 18002613, compound

Product 1

HCID 12074627HCID 12074627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 1 was repeated using 2-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), methyl 7-(pyridin-4-yl)heptanoate (2.0 eq., prepared in Synthetic Example 15) and LDA (2.0 eq.) to obtain 1-(3-nitrophenyl)-3-[5-(pyridin-4-yl)pentyl]-1,8-naphthyridin-2(1H)-one, mp 188.8 to 189.6° C./DMF, wherein the product was purified through silica gel column chromatography and recrystallization.

Sources & evidence

ORD record
ord-b0ac7d36fd1d477686b9abc08fcf2161
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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