2-Amino-4-phenylthiazole → 2-Benzyl-N-(4-phenyl-thiazol-2-yl)-malonamic acid ethyl ester

HRID 2380762Notes

Reaction equation

HRID 2380762 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=O)[CH3:2].Cl.CN(C)CCCN=C=NCC.[C:29]1([C:35]2[N:36]=[C:37]([NH2:40])[S:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([NH:40][C:37]1[S:38][CH:39]=[C:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:36]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 403022-Amino-4-phenylthiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28848672-Benzyl-malonic acid monoethyl ester

Product 1

HCID 593640372-Benzyl-N-(4-phenyl-thiazol-2-yl)-malonamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 2-Benzyl-malonic acid monoethyl ester (150 mg, 0.67 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.74 mmol) in DMF (4 mL) at 25° C. was added 4-phenyl-thiazol-2-ylamine (119 mg, 0.67 mmol), the resulting mixture was stirring at 25° C. for overnight and concentrated in vacuo, and the residue was dissolved in CH2Cl2 (20 mL) was washed with 5% NaHCO3, dried with MgSO4 and concentrated in vacuo. The residue was purified by HPLC. The product was obtained 170 mg (67%) as white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (20 mL)
  3. washwas washed with 5% NaHCO3
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC
  7. customThe product was obtained 170 mg (67%) as white solid

Sources & evidence

ORD record
ord-06a8605dd28f452196db886c1e1db1ac
Source dataset
uspto-grants-2012_09
Patent number
US08257931B2

Reaction notes

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