Acetic Acid → Ethyl 5-[2-[(4-chlorophenyl)amino]-1-(4-methylpiperazin-1-yl)-2-oxoethyl]thiophene-2-carboxylate

HRID 1919885Notes

Reaction equation

HRID 1919885 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1)=O.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]#[C-:28])=[CH:23][CH:22]=1.C(O)(=[O:31])C>C(O)C(F)(F)F>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH:1]([C:3]2[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=2)[N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 746704-Chlorophenyl isocyanideHCID 10797570Ethyl 5-formylthiophene-2-carboxylate

Product 1

HCID 57611900Ethyl 5-[2-[(4-chlorophenyl)amino]-1-(4-methylpiperazin-1-yl)-2-oxoethyl]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

Ethyl 5-formylthiophene-2-carboxylate (0.50 g, 2.71 mmol) was made 2.25 M in anhydrous trifluoroethanol and to this stirring solution was added N-methylpiperazine (0.33 g, 3.26 mmol), 1-chloro-4-isocyanobenzene (0.45 g, 3.26 mmol) and acetic acid (0.20 g, 3.26 mmol). The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo then purified by MPLC to give the desired product. MS: cal'd 422, 424 (MH+), exp 422, 424 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthen purified by MPLC

Sources & evidence

ORD record
ord-540ccf93ef494caea6b5ba8d356c35ac
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

Loading…