2-(Dimethylamino)ethanol → N-(6-(6-(2-(dimethylamino)ethoxy)-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077536Notes

Reaction equation

HRID 2077536 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:28]=[CH:27][C:19]3[N:20]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[S:22][C:18]=3[CH:17]=2)=[CH:12][C:11]=1[NH:29][CH:30]([CH3:32])[CH3:31]>CS(C)=O>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:28]=[CH:27][C:19]3[N:20]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[S:22][C:18]=3[CH:17]=2)=[CH:12][C:11]=1[NH:29][CH:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 57585083HCID 57585083, compound

Product 1

HCID 57584995N-(6-(6-(2-(dimethylamino)ethoxy)-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamideYield 34%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(dimethylamino)ethanol (140.2 mg, 1.573 mmol) was dissolved in DMSO (1.5 ml) and sodium hydride (85.8 mg, 60% in mineral oil, 2.15 mmol) was added. The reaction was stirred under nitrogen at room temperature for almost 2 hours, and then N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (102.5 mg, 0.2840 mmol) was added. The flask was put in a preheated oil bath (105° C.) and stirred under nitrogen (a reflux condenser was added after about 5 minutes). After 90 minutes, the reaction was cooled to room temperature and quenched with water. The reaction was extracted with 10:1 DCM/MeOH, but the product is water soluble, so the organic and aqueous phases were combined, concentrated, and filtered through a pad of Celite® (diatomaceous earth), which was washed with DCM and MeOH. This filtrate was concentrated and purified on a silica gel column (20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH to 10:1 DCM/2 N ammonia in MeOH) to afford N-(6-(6-(2-(dimethylamino)ethoxy)-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (39.4 mg, 34% yield). MS (ESI pos. ion) m/z: 414. Calculated exact mass for C21H27N5O2S 413.

Workup

  1. customThe flask was put in a preheated oil bath
  2. stirring(105° C.) and stirred under nitrogen (a reflux condenser was added after about 5 minutes)
  3. waitAfter 90 minutes
  4. temperaturethe reaction was cooled to room temperature
  5. customquenched with water
  6. extractionThe reaction was extracted with 10:1 DCM/MeOH
  7. concentrationconcentrated
  8. filtrationfiltered through a pad of Celite® (diatomaceous earth), which
  9. washwas washed with DCM and MeOH
  10. concentrationThis filtrate was concentrated
  11. custompurified on a silica gel column (20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH to 10:1 DCM/2 N ammonia in MeOH)

Sources & evidence

ORD record
ord-ecf24af3e52e4f6b831229f731c27839
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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