Lithium diisopropylamide → HCID 18002640, compound

HRID 478762Notes

Reaction equation

HRID 478762 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].[S:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[CH2:28][CH2:29][CH2:30][CH2:31][C:32](OC)=[O:33].[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:31]([CH2:30][CH2:29][CH2:28][C:20]3[S:19][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=3)[C:32]2=[O:33])[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 18002644Methyl 5-(1,3-benzothiazol-2-yl)pentanoate

Product 1

HCID 18002640HCID 18002640, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 1 was repeated using 2-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), methyl 5-(2-benzo-thiazolyl)pentanoate (1.5 eq., prepared in Synthetic Example 23) and LDA (1.5 eq.) to obtain 1-(3-nitrophenyl)-3-[3-(benzothiazol-2-yl)propyl]-1,8-naphthyridin-2(1H)-one, mp 185 to 186° C./DMF, wherein the product was purified through flash column chromatography and recrystallization.

Sources & evidence

ORD record
ord-e0add4630994478ea6597bc2e0c1aed4
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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