Lithium diisopropylamide → HCID 21936622, compound

HRID 1241714Notes

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][CH:22]=[C:21]([CH2:25][CH2:26][CH2:27][CH2:28][C:29](OCC)=[O:30])[N:20]=1.[Li+].CC([N-]C(C)C)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:28]([CH2:27][CH2:26][CH2:25][C:21]3[N:20]=[N:19][CH:24]=[CH:23][CH:22]=3)[C:29]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 3

HCID 2724682Lithium diisopropylamide

HCID 121149522-(3-Nitro-phenylamino)-pyridine-3-carbaldehyde

HCID 21936624HCID 21936624, compound

Product 1

HCID 21936622HCID 21936622, compoundYield 4.9%

Procedure

The procedure of Example 1 was repeated using 2-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), ethyl 5-(pyridazin-3-yl)pentanoate (1.2 eq., prepared in Synthetic Example 6) and LDA (1.2 eq.) to obtain 1-(3-nitrophenyl)-3-[3-(pyridazin-3-yl)propyl]-1,8-naphthyridin-2(1H)-one (yield, 4.9%). The product was purified through flash column chromatography and recrystallization (mp 234–235° C./DMF).

Sources & evidence

ORD record: ord-faa712e372fe429a94b3fd4d817f0799
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115623B2

Reaction notes

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