Lithium diisopropylamide → 1-(2,1,3-benzothiadiazol-5-yl)-3-[3-(pyridin-2-yl)propyl]-1,8-naphthyridin-2(1H)-one

HRID 1241713Notes

Reaction equation

HRID 1241713 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([NH:10][C:11]3[N:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH:13]=O)[CH:7]=[CH:6][C:5]=12.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][CH2:27][CH2:28][C:29](OCC)=[O:30].[Li+].CC([N-]C(C)C)C>>[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([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:20]4[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=4)[C:29]3=[O:30])[CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11241218Ethyl 5-(pyridin-2-yl)pentanoateHCID 219366412-(2,1,3-Benzothiadiazol-5-ylamino)nicotinaldehyde

Product 1

HCID 129858651-(2,1,3-benzothiadiazol-5-yl)-3-[3-(pyridin-2-yl)propyl]-1,8-naphthyridin-2(1H)-oneYield 27%

Procedure

The procedure of Example 1 was repeated using 2-(2,1,3-benzothiadiazol-5-ylamino)nicotinaldehyde (1.0 eq., prepared in Synthetic Example 1a)), ethyl 5-(pyridin-2-yl)pentanoate (1.5 eq., prepared in Synthetic Example 4) and LDA (1.5 eq.) to obtain 1-(2,1,3-benzothiadiazol-5-yl)-3-[3-(pyridin-2-yl)propyl]-1,8-naphthyridin-2(1H)-one (yield, 27%). The product was purified through flash column chromatography and recrystallization (mp 169.5–170.5° C./DMF).

Sources & evidence

ORD record
ord-cd6643704d6c40fba288af050c82ca1f
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

Loading…