HCID 117667619, compound → HCID 117667801, compound

HRID 712684Notes

Reaction equation

HRID 712684 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH:24]=[O:25])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.[CH:26]([Mg]Cl)([CH3:28])[CH3:27]>C1COCC1>[CH3:27][CH:26]([CH3:28])[CH:24]([C:22]1[CH:21]=[N:20][CH:19]=[C:18]([C:14]2[CH:15]=[N:16][C:17]3[NH:8][CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[CH:23]=1)[OH:25]

Participants

4

Reactant 2

HCID 117667619HCID 117667619, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 117667801HCID 117667801, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) suspension of 6-(5-formyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (125 mg, 0.37 mmol) in THF (1 mL) is added a solution of isopropylmagnesium chloride in THF (1.3M, 850 μL, 1.1 mmol). The resultant mixture is stirred warming to room temperature for 3 h. The reaction is quenched with saturated aqueous ammonium chloride solution and is extracted with EtOAc. The combined organic extracts are washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure. The residue is taken up in MeOH (1 mL) and 4N HCl in 1,4-dioxane (1 mL) is added. The reaction is stirred at room temperature for 16 h then is concentrated to provide 2-methyl-1-[5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-propan-1-ol (124 mg) as the dihydrochloride salt.

Workup

  1. temperatureTo a cooled
  2. customThe reaction is quenched with saturated aqueous ammonium chloride solution
  3. extractionis extracted with EtOAc
  4. washThe combined organic extracts are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. addition4N HCl in 1,4-dioxane (1 mL) is added
  8. concentrationthen is concentrated

Sources & evidence

ORD record
ord-91275a413be64432a76ceff33ba9c7f8
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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