Triethylamine → 3-{4-[(4S)-4-benzyl-2-oxo-1,3-thiazolidin-3-yl]-4-oxobutyl}-1,2,3-benzotriazin-4(3H)-one

HRID 83994

Reaction equation

HRID 83994 reaction equation
[CH2:1]([C@H:8]1[CH2:12][S:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.C(N=C=N)C.[O:27]=[C:28]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[N:30][N:29]1[CH2:38][CH2:39][CH2:40][C:41](O)=[O:42]>ClCCl.CN(C)C1C=CN=CC=1.O>[CH2:1]([C@H:8]1[CH2:12][S:11][C:10](=[O:13])[N:9]1[C:41](=[O:42])[CH2:40][CH2:39][CH2:38][N:29]1[C:28](=[O:27])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[N:30]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 47367434-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)butanoic acidHCID 21883477Ethylcarbodiimide hydrochlorideHCID 25417901(4S)-4-Benzyl-1,3-thiazolidin-2-one

Product 1

HCID 667150953-{4-[(4S)-4-benzyl-2-oxo-1,3-thiazolidin-3-yl]-4-oxobutyl}-1,2,3-benzotriazin-4(3H)-one

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the compound obtained from step c above (2.1 g) in dichloromethane (25 mL) cooled to 0° C., 4-dimethylaminopridine (0.334 g) and triethylamine (5.7 mL) were added. After stirring the reaction mixture for 10 minutes, 1-β-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (3.9 g) and 4-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)butanoic acid (3 g) were added, and the reaction mixture was stirred at room temperature for 14 hours. Dichloromethane and water were added to the reaction mixture. The organic layer was separated, washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to obtain a residue which was purified by column chromatography over silica gel using 25% ethyl acetate in hexane as eluant to afford the title compound (4.4 g). Mass (m/z): 409.16

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 14 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. customto obtain a residue which
  7. customwas purified by column chromatography over silica gel using 25% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-0d599c1a59514fb1acac3acaa79a94cd
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Linked notes

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