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Sodium Hydroxide → HCID 67511946, compound

HRID 2404448
Notes
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Reaction equation

HRID 2404448 reaction equation
Cl.[CH3:2][NH2:3].C[Al](C)C.C[O:9][C:10](=O)[CH2:11][S:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([C:28]2[S:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[O:20][CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[CH:14]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[S:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=[C:28]1[CH:19]([O:20][CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1)[C:15]1[CH:14]=[C:13]([S:12][CH2:11][C:10]([NH:3][CH3:2])=[O:9])[CH:18]=[CH:17][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6364545Methylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 66835983HCID 66835983, compound

Product 1

HCID 67511946HCID 67511946, compound

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 1140TolueneSolvent3×

Conditions

Temperature
60 °C

Procedure

To a solution of methylamine hydrochloride (76 mg) in toluene (2 mL) is added a 2N solution of trimethylaluminum in toluene. The reaction mixture is heated at 60° C. for 1 hour. Then a solution of {3-[(benzothiazol-2-yl)(1-methylpiperidin-4-yloxy)-methyl]phenylsulfanyl}acetic acid methyl ester (50 mg) in toluene (1 mL) is added. The reaction mixture is heated at 60° C. for 24 hours. Water is added to the reaction mixture, pH is adjusted to 10 with a solution of sodium hydroxide, and the mixture is filtered on celite. The filtrate is extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (toluene/acetone/triethylamine 80/20/0.2) to give 2-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}-N-methylacetamide.

Workup

  1. temperatureThe reaction mixture is heated at 60° C. for 24 hours
  2. filtrationthe mixture is filtered on celite
  3. extractionThe filtrate is extracted with ethyl acetate
  4. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography (toluene/acetone/triethylamine 80/20/0.2)

Sources & evidence

ORD record
ord-d867bdce2dde4f5ca0349232f40bab49
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08802664B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes