Pentamethylbenzene → HCID 72303454, compound

HRID 1747082Notes

Reaction equation

HRID 1747082 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:13]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[Cl:38])[CH:12]2[C:39]([NH:41][O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)=[O:40])C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1>FC(F)(F)C(O)=O>[Cl:38][C:32]1[CH:33]=[C:34]([Cl:37])[CH:35]=[CH:36][C:31]=1[CH:13]1[CH:12]([C:39]([NH:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=2)=[O:40])[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[C:15](=[O:19])[N:14]1[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 12784PentamethylbenzeneHCID 72303507HCID 72303507, compound

Product 1

HCID 72303454HCID 72303454, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 400 mg of (3RS,4RS)-6-(benzyloxy)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-N-(pyridin-2-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-4-carboxamide and 245 mg of pentamethylbenzene in 15 ml of trifluoroacetic acid was stirred at room temperature overnight. The trifluoroacetic acid was evaporated under reduced pressure, and ethyl acetate and water were added thereto to carry out a liquid separation operation. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was solidified with ethyl acetate-isopropyl alcohol and collected by filtration to obtain 350 mg of (3RS,4RS)-3-(2,4-dichlorophenyl)-6-hydroxy-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-N-(pyridin-2-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-4-carboxamide as a white solid.

Workup

  1. customThe trifluoroacetic acid was evaporated under reduced pressure, and ethyl acetate and water
  2. additionwere added
  3. customa liquid separation operation
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4c8c56940e6f430f892c3304b929bbe9
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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