Dichloromethane → HCID 54704649, compound

HRID 2214710Notes

Reaction equation

HRID 2214710 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22]C=1Cl)[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][N:33]=[C:34]=[O:35].[CH2:36]([Cl:38])Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:36]=1[Cl:38])[CH2:5][N:6]([CH3:20])[C:7]([C:9]1[CH2:10][N:11]([CH2:16][CH2:17][N:18]([CH3:19])[C:34]([NH:33][CH3:32])=[O:35])[C:12](=[O:15])[C:13]=1[OH:14])=[O:8]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 54698194N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-[2-(methylamino)ethyl]-5-oxo-2H-pyrrole-3-carboxamide2×

Product 1

HCID 54704649HCID 54704649, compoundYield 52%

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) (155 mg, 0.379 mmol) in CH2Cl2 (5 mL) was added Et3N (0.14 mL, 1.0 mmol) followed by methyl isocyanate (29 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 product were combined, concentrated and lyophilized to give the title compound as a white powder (107.6 mg, 52% yield). 1HNMR (500 MHz, CDCl3) δ: 11.56 (1H, br s), 7.41 (1H, d, J=8.2 Hz), 7.34 (1H, s), 7.10 (1H, d, J=8.2 Hz), 4.66 (1H, br s), 4.57 (2H, s), 4.28 (2H, s), 3.62 (2H, t, J=5.8 Hz), 3.56 (2H, t, J=5.8 Hz), 3.02 (3H, s), 2.89 (3H, s), 2.70 (3H, s). HRMS calcd for C18H23Cl2N4O4 (M+H): 429.1096. found: 429.1082.

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 product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6da256ae26e4a69a13a425cc35e0457
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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