Tetrahydrofuran → N-[6-(4-Chlorophenyl)-7-(2,4-dichlorophenyl)-3-(1-hydroxyethyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

HRID 13804Notes

Reaction equation

HRID 13804 reaction equation
[C:1]([C:4]1[C:5](=[O:34])[N:6]([CH3:33])[C:7]2[C:12]([C:13]=1[NH:14][C:15](=[O:17])[CH3:16])=[CH:11][C:10]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[C:9]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])[N:8]=2)(=[O:3])[CH3:2].C1COCC1.[BH4-].[Na+]>CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:10]2[CH:11]=[C:12]3[C:7](=[N:8][C:9]=2[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:6]([CH3:33])[C:5](=[O:34])[C:4]([CH:1]([OH:3])[CH3:2])=[C:13]3[NH:14][C:15](=[O:17])[CH3:16])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 11386747Naphthyridinone

Product 1

HCID 11283741N-[6-(4-Chlorophenyl)-7-(2,4-dichlorophenyl)-3-(1-hydroxyethyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 1 (65 mg), THF (3 mL), MeOH (0.33 mL) and NaBH4 (9.6 mg) were combined at room temperature. After 7 minutes the reaction was concentrated and then dissolved in EtOAc before washing with water and drying (Na2SO4). The concentrated residue was purified by preparative TLC (silica gel) eluted with EtOAc affording the title compound. HPLC/MS: 515.9 (M+1), 517.9 (M+3); Rt=3.68 min.

Workup

  1. customwere combined at room temperature
  2. concentrationAfter 7 minutes the reaction was concentrated
  3. dissolutiondissolved in EtOAc
  4. washbefore washing with water
  5. dry with materialdrying (Na2SO4)
  6. customThe concentrated residue was purified by preparative TLC (silica gel)
  7. washeluted with EtOAc affording the title compound

Sources & evidence

ORD record
ord-b5b31bbe1b2e446d94d4b4c91c35140c
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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