Sodium Hydroxide → n-Isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

HRID 351732Notes

Reaction equation

HRID 351732 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][Si](C)(C)C)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[CH:25])[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22714290n-Isopropyl-1-[3-(trimethylsilylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

Product 1

HCID 9880627n-Isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude product from Step 1 was dissolved in methanol (12 mL/mmol) and 1N aqueous sodium hydroxide was added (3 eq), resulting in a suspension. The suspension mixture was stirred at room temperature for 2 hours and the methanol was evaporated. The resulting aqueous suspension was diluted with water and the product was extracted out with ethyl acetate. The crude product was chromatographed on silica gel eluting with 10% ether in methylene chloride to afford the N-isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid.

Workup

  1. customresulting in a suspension
  2. customthe methanol was evaporated
  3. additionThe resulting aqueous suspension was diluted with water
  4. extractionthe product was extracted out with ethyl acetate
  5. customThe crude product was chromatographed on silica gel eluting with 10% ether in methylene chloride

Sources & evidence

ORD record
ord-269f20f8fa804628afc43a0d977e6a13
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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