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Triethylamine → HCID 86707196, compound

HRID 715885
Notes
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Reaction equation

HRID 715885 reaction equation
[F:1][C:2]1([F:48])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:33][NH:34][CH3:35])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:36]([F:47])[C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:56][S:57](Cl)(=[O:59])=[O:58].C(=O)([O-])O.[Na+]>ClCCl>[F:48][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:22][CH2:23][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:33][N:34]([CH3:35])[S:57]([CH3:56])(=[O:59])=[O:58])=[CH:29][N:28]=4)[CH2:25][CH2:26]3)[C:9]=2[CH:36]([F:47])[C:37]2[CH:38]=[CH:39][C:40]([C:43]([F:45])([F:44])[F:46])=[CH:41][CH:42]=2)[CH2:6][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86682466HCID 86682466, compound

Product 1

HCID 86707196HCID 86707196, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 65 mg (95 μmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-(1-{5-[(methylamino)methyl]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Example 58, in 0.2 ml of dichloromethane, 30 μl (0.19 mmol) of triethylamine and 8 μl (0.1 mmol) of methanesulfonyl chloride were added, and the reaction solution was stirred at room temperature for 1 hour. After completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was poured into the reaction solution and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=100/0-40/60 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 37 mg of the title compound as a white solid (yield: 52%).

Workup

  1. additionwas poured into the reaction solution
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c2d9eaad9fe4914adef527aa78fa910
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187450B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes