Dimethylamine → HCID 74344756, compound

HRID 2375319Notes

Reaction equation

HRID 2375319 reaction equation
[CH3:1][NH:2][CH3:3].CCCCCC.[C:10]([C:14]1[NH:15][C:16](=[C:19]([C:33]#[N:34])[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28][C:29]([O:31]C)=O)[N:21]=2)[S:17][CH:18]=1)([CH3:13])([CH3:12])[CH3:11].O>ClCCCl.C(Cl)Cl>[C:10]([C:14]1[NH:15][C:16](=[C:19]([C:33]#[N:34])[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28][C:29]([N:2]([CH3:3])[CH3:1])=[O:31])[N:21]=2)[S:17][CH:18]=1)([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 8058HexaneHCID 69314056HCID 69314056, compound

Product 1

HCID 74344756HCID 74344756, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of dimethylamine (0.051 mL, 1 mmol) in DCE was added a solution of TMA 2M in hexane (499 mmol, 1 mmol) and the mixture was stirred 30 min at r.t. To this solution was added a solution of methyl N-{4-[(4-tert-butyl-1,3-thiazol-2(3H)-ylidene)(cyano)methyl]pyrimidin-2-yl}-beta-alaninate (72 mg, 0.2 mmol) in DCE and the mixture was refluxed under inert atmosphere overnight then stirred for a week at r.t. The mixture was diluted with DCM then water was added. The suspension was filtered through celite. The filtrate was washed with aqueous NaHCO3 5% (×2) then brine and it was dried over MgSO4. The solvent was removed under reduced pressure affording the title compound as yellow solid (HPLC max plot 86%).

Workup

  1. temperaturethe mixture was refluxed under inert atmosphere overnight
  2. stirringthen stirred for a week at r.t
  3. filtrationThe suspension was filtered through celite
  4. washThe filtrate was washed with aqueous NaHCO3 5% (×2)
  5. dry with materialbrine and it was dried over MgSO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2aea5c96da35404b9d473582a381560e
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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