Sodium Hydroxide → HCID 67511946, compound

HRID 572859Notes

Reaction equation

HRID 572859 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

Participants

7

Reactant 4

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

Product 1

HCID 67511946HCID 67511946, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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-15cbbe4bbcf449ef9c2f7ec478fdc12b
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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