Dimethylamine → HCID 86594581, compound

HRID 1744147Notes

Reaction equation

HRID 1744147 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]#[N:27])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[N:13][S:14][CH:15]=2)=[CH:7][CH:6]=1)=[O:4].[CH3:28][NH:29][CH3:30].C([O-])(O)=O.[Na+]>CN(C=O)C.C1COCC1>[C:26]([CH2:25][NH:24][C:22](=[O:23])[C@H:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:16][C:12]1[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:29]([CH3:30])[CH3:28])=[CH:6][CH:7]=2)=[CH:15][S:14][N:13]=1)#[N:27]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 86594582HCID 86594582, compound

Product 1

HCID 86594581HCID 86594581, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

N2-{4-[4-(bromoacetyl)phenyl]isothiazol-3-yl}-N1-(cyanomethyl)leucinamide (29 mg, 0.064 mmol) was dissolved in DMF (0.6 mL) and dimethylamine (0.13 mL of a 2 M solution in THF, 0.26 mmol) was added. The reaction mixture was stirred until disappearance of the starting material was observed by TLC (˜1 h). Aqueous sat. NaHCO3 was added, the product was extracted with EtOAc (3×), dried over MgSO4, concentrated in vacuo and purified by flash chromatography with dichloromethane, methanol and ammonium hydroxide to yield N1-(cyanomethyl)-N2-{4-[4-(N,N-dimethylglycyl)phenyl]isothiazol-3-yl} leucinamide.

Workup

  1. customwas observed by TLC (˜1 h)
  2. extractionthe product was extracted with EtOAc (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography with dichloromethane, methanol and ammonium hydroxide

Sources & evidence

ORD record
ord-c7ca5a3f5f1a48cbb2b5c3fc88c2bf48
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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