Triethylamine → HCID 86613803, compound

HRID 2378125Notes

Reaction equation

HRID 2378125 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[CH:10]([N:21]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)[C:22]#[N:23])[CH2:9][CH:8]1[CH2:39][CH3:40])=[O:6])([CH3:3])[CH3:2].Cl.N[OH:43].[CH2:44]([N:46](CC)CC)[CH3:45]>CCO>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=2)[C@H:10]([N:21]([CH2:24][C:25]2[CH:26]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=2)[C:22]2[N:46]=[C:44]([CH3:45])[O:43][N:23]=2)[CH2:9][C@@H:8]1[CH2:39][CH3:40])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 77910708HCID 77910708, compound

Product 1

HCID 86613803HCID 86613803, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[(3,5-bis-trifluoromethyl-benzyl)-cyano-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (from Example 9) (250 mg, 0.429 mmol) in EtOH (2.6 mL), add hydroxylamine hydrochloride (75 mg, 1.07 mmol) and triethylamine (0.150 mL, 1.07 mmol) at room temperature. Stir the reaction mixture at 80° C. overnight. Cool the mixture and remove the solvents under reduced pressure. Dilute the residue with ethyl acetate and add brine. Separate the layers, dry the organic phase over magnesium sulfate, filter, and concentrate in vacuo. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (84 mg, 32%). MS (ES+): 616 (M+H).

Workup

  1. temperatureCool the mixture
  2. customremove the solvents under reduced pressure
  3. additionDilute the residue with ethyl acetate
  4. additionadd brine
  5. customSeparate the layers
  6. dry with materialdry the organic phase over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the residue by flash chromatography
  10. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-13c7f46bc2174aee8883e8c577992ab1
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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