Triethylamine → 4-Hydroxy-1-[2-(methanesulfonyl-methyl-amino)-ethyl]-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methyl-amide

HRID 2214709Notes

Reaction equation

HRID 2214709 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]([CH3:20])[C:7]([C:9]1[CH2:10][N:11]([CH2:16][CH2:17][NH:18][CH3:19])[C:12](=[O:15])[C:13]=1[OH:14])=[O:8].CCN(CC)CC.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]([CH3:20])[C:7]([C:9]1[CH2:10][N:11]([CH2:16][CH2:17][N:18]([S:33]([CH3:32])(=[O:35])=[O:34])[CH3:19])[C:12](=[O:15])[C:13]=1[OH:14])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54698194N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-[2-(methylamino)ethyl]-5-oxo-2H-pyrrole-3-carboxamide2×

Product 1

HCID 547046504-Hydroxy-1-[2-(methanesulfonyl-methyl-amino)-ethyl]-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methyl-amideYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-hydroxy-1-(2-methylamino-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methyl-amide (Compound 15) (150 mg, 0.367 mmol) in CH2Cl2 (5 mL) was added Et3N (0.14 mL, 1.0 mmol) followed by methanesulfonyl chloride (38 μL, 0.5 mmol) at room temperature. After 1 h, the reaction mixture was concentrated and the resulting residue was dissolved in methanol and purified by preparative HPLC on a C18 column using water/methanol-(0.1% TFA) as eluent. The fractions containing the desired product were combined, concentrated and lyophilized to give the title compound as a white powder (21.3 mg, 13% yield). 1HNMR (500 MHz, CDCl3) δ: 7.42 (1H, d, J=8.2 Hz), 7.35 (1H, s), 7.11 (1H, d, J=8.2 Hz), 4.58 (2H, s), 4.29 (2H, s), 3.71 (2H, t, J=5.8 Hz), 3.38 (2H, t, J=5.8 Hz), 3.02 (3H, s), 2.89 (3H, s), 2.78 (3H, s). HRMS calcd for C17H22Cl2N3O5S (M+H): 450.0657. found: 450.0658.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionthe resulting residue was dissolved in methanol
  3. custompurified by preparative HPLC on a C18 column
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2272c422f37d4ee7af964be1788d670b
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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