p-Toluenesulfonic acid → HCID 69084124, compound

HRID 594662Notes

Reaction equation

HRID 594662 reaction equation
[NH2:1][C:2]1[C:3]([OH:28])=[C:4]([CH:10]2[N:15]([CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)[C:14](=[O:27])[CH2:13][CH2:12][CH2:11]2)[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[CH3:29][C:30]1C=CC(S(O)(=O)=O)=CC=1.C(OCC)(OCC)(OCC)C>CCOC(C)=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:29]([CH3:30])[O:28][C:3]=2[C:4]=1[CH:10]1[N:15]([CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[C:14](=[O:27])[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 66221Triethyl orthoacetateHCID 69081808HCID 69081808, compound

Product 1

HCID 69084124HCID 69084124, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(3-amino-2-hydroxy-6-methoxyphenyl)-1-(quinolin-2-ylmethyl)piperidin-2-one (100 mg; 0.26 mmol), commercially available p-TsOH (2 mg; 0.01 mmol), and commercially available triethyl orthoacetate (290 mg; 1.69 mmol) was refluxed (100° C.) for 25 min. After cooling to rt, AcOEt was added, and the obtained mixture was filtered over a pad of celite. The filtrate was then washed with water and brine, and the mixed aq. layers were further extracted with AcOEt. The mixed organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by FC (DCM/MeOH=20/1) afforded the target compound. LC-MS (conditions A): tR=0.54 min.; [M+H]+: 401.73 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe obtained mixture was filtered over a pad of celite
  3. washThe filtrate was then washed with water and brine
  4. extractionthe mixed aq. layers were further extracted with AcOEt
  5. dry with materialThe mixed organic layers were then dried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customSubsequent purification by FC (DCM/MeOH=20/1)
  9. customafforded the target compound

Sources & evidence

ORD record
ord-4a12fcf9d4444a1cbf5b2488aa70fb8f
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

Loading…