Lithium diisopropylamide → 1-(2,1,3-benzothiadiazol-4-yl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

HRID 1241722Notes

Reaction equation

HRID 1241722 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[C:9]([NH:10][C:11]3[N:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH:13]=O)=[CH:8][CH:7]=[CH:6][C:5]=12.[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][C:29](OCC)=[O:30])=[CH:21][CH:20]=1.[Li+].CC([N-]C(C)C)C>>[N:1]1[S:2][N:3]=[C:4]2[C:9]([N:10]3[C:11]4[C:12](=[CH:15][CH:16]=[CH:17][N:18]=4)[CH:13]=[C:28]([CH2:27][CH2:26][CH2:25][C:22]4[CH:21]=[CH:20][N:19]=[CH:24][CH:23]=4)[C:29]3=[O:30])=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11241221Ethyl 5-(4-pyridyl)pentanoateHCID 219366372-(2,1,3-Benzothiadiazol-4-ylamino)nicotinaldehyde

Product 1

HCID 219366421-(2,1,3-benzothiadiazol-4-yl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-oneYield 7%

Procedure

The procedure of Example 1 was repeated using 2-(2,1,3-benzothiadiazol-4-ylamino)nicotinaldehyde (1.0 eq.; prepared in Synthetic Example 1c)), ethyl 5-(pyridin-4-yl)pentanoate (1.5 eq.; prepared in Synthetic Example 2) and LDA (1.5 eq.) to obtain 1-(2,1,3-benzothiadiazol-4-yl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (yield 7%). The target product was purified through flash column chromatography and recrystallization, mp 191–192° C./DMF.

Sources & evidence

ORD record
ord-5296f11fc85741b09ba5b7f1c7ae08b9
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

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