Isopropylamine → HCID 10274114, compound

HRID 1072296Notes

Reaction equation

HRID 1072296 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]([N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][N:24]=4)[C:19](=[O:26])[C:18]([C:27](O)=[O:28])=[CH:17]3)[CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2].S(Cl)(Cl)=O.[CH:34]([NH2:37])([CH3:36])[CH3:35]>O1CCCC1>[CH:34]([NH:37][C:27]([C:18]1[C:19](=[O:26])[C:20]2[C:25](=[N:24][CH:23]=[CH:22][CH:21]=2)[N:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)[CH:11]=2)[CH:17]=1)=[O:28])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 24386Thionyl ChlorideHCID 22392001HCID 22392001, compound

Product 1

HCID 10274114HCID 10274114, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-[3-(3-ethoxyphenyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylic acid from Step 2 and thionyl chloride (4 eq) in tetrahydrofuran (10 ml/mmol) was refluxed for 45 minutes, then evaporated. The residue was dissolved in the same volume of tetrahydrofuran, isopropylamine (5 eq) was added and the mixture was stirred at room temperature for 18 hours. After quenching with saturated aqueous ammonium chloride solution, the resulting mixture was partitioned between ethyl acetate and water, and the product from the organic phase was chromatographed on silica gel eluting with 10% ether in methylene chloride to afford the N-Isopropyl-1-[3-(3-ethoxyphenyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid.

Workup

  1. temperaturewas refluxed for 45 minutes
  2. customevaporated
  3. additionwas added
  4. customAfter quenching with saturated aqueous ammonium chloride solution
  5. customthe resulting mixture was partitioned between ethyl acetate and water
  6. customthe product from the organic phase was chromatographed on silica gel eluting with 10% ether in methylene chloride

Sources & evidence

ORD record
ord-38e7f9d97e684180a5565add8f77b6d2
Source dataset
uspto-grants-2005_06
Patent number
US06909002B2

Reaction notes

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