p-Toluenesulfonic acid → HCID 53329179, compound

HRID 1028995Notes

Reaction equation

HRID 1028995 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.C([NH:16][C:17]1[C:26]([CH:27](O)[CH2:28][CH2:29][CH2:30][CH2:31][OH:32])=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[C:41]([N:43]3[CH2:47][CH2:46][CH2:45][CH2:44]3)=[O:42])[CH:23]=2)[N:18]=1)(C)(C)C>C1(C)C=CC=CC=1>[NH2:16][C:17]1[C:26]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][O:32]2)=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[C:41]([N:43]3[CH2:44][CH2:45][CH2:46][CH2:47]3)=[O:42])[CH:23]=2)[N:18]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 71253418HCID 71253418, compound

Product 1

HCID 53329179HCID 53329179, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

TsOH (0.109 g, 0.572 mmol) was added to a solution of (2-(2-(tert-butylamino)-3-(1,5-dihydroxypentyl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone (0.070 g, 0.143 mmol) in toluene (2.0 mL) and the reaction was refluxed for 1.5 h. The reaction was concentrated and diluted with 10% sodium carbonate and extracted with dichloromethane. The combined organic extracts were washed with saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material which was purified by silica gel chromatography by eluting with 100% EtOAc followed by 1:20 2M NH3 in MeOH/dichloromethane, to provide (2-(2-amino-3-(tetrahydro-2H-pyran-2-yl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone. MS (ESI, pos. ion) m/z: 416 (M+1).

Workup

  1. temperaturethe reaction was refluxed for 1.5 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with 10% sodium carbonate
  4. extractionextracted with dichloromethane
  5. washThe combined organic extracts were washed with saturated sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customto give the crude material which
  10. customwas purified by silica gel chromatography
  11. washby eluting with 100% EtOAc

Sources & evidence

ORD record
ord-a2fb936914684c9b97908d94c3942e63
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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