Water → 1-(2,1,3-benzothiadiazol-5-yl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

HRID 1241711Notes

Reaction equation

HRID 1241711 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=O)=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.[N:24]1[S:25][N:26]=[C:27]2[CH:32]=[C:31]([NH:33][C:34]3[N:41]=[CH:40][CH:39]=[CH:38][C:35]=3[CH:36]=O)[CH:30]=[CH:29][C:28]=12.O>C1COCC1>[N:24]1[S:25][N:26]=[C:27]2[CH:32]=[C:31]([N:33]3[C:34]4[C:35](=[CH:38][CH:39]=[CH:40][N:41]=4)[CH:36]=[C:10]([CH2:9][CH2:8][CH2:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[C:11]3=[O:13])[CH:30]=[CH:29][C:28]=12

Participants

6

Reactant 4

HCID 962WaterHCID 2724682Lithium diisopropylamideHCID 11241221Ethyl 5-(4-pyridyl)pentanoateHCID 219366412-(2,1,3-Benzothiadiazol-5-ylamino)nicotinaldehyde

Product 1

HCID 129858631-(2,1,3-benzothiadiazol-5-yl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-oneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 5-(pyridin-4-yl)pentanoate (1.5 eq., prepared in Synthetic Example 2) was dissolved in dry THF. To the solution was added LDA (2M solution, 1.5 eq.) at −78° C. or below in a dry ice-methanol bath under nitrogen atmosphere while stirring and the mixture was stirred for 1 hour. Next, to the reaction mixture was added dropwise a solution of 2-(2,1,3-benzothiadiazol-5-ylamino)-nicotinaldehyde (1.0 eq., prepared in Synthetic Example 1a)) in THF and the resultant mixture was stirred for 2 hours at −78° C. and then continued to stir for 24 hours until it reached room temperature. The reaction mixture was treated with water, and extracted with methylene chloride. The extract was dried, and evaporated. To the residue was added ethyl acetate to form crystals. Thus, 1-(2,1,3-benzothiadiazol-5-yl) -3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one was obtained. The product was purified through flash column chromatography and recrystallization (yield: 43%, mp 193.5–195.5° C./DMF).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringto stir for 24 hours until it
  3. customreached room temperature
  4. extractionextracted with methylene chloride
  5. customThe extract was dried
  6. customevaporated
  7. additionTo the residue was added ethyl acetate
  8. customto form crystals

Sources & evidence

ORD record
ord-634032b8a0c64e8c8499c10bdb871e10
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

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