Dichloromethane → HCID 58699859, compound

HRID 2214711Notes

Reaction equation

HRID 2214711 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.C[Si]([N:36]=[C:37]=[O:38])(C)C.[CH2:39]([Cl:41])Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:39]=1[Cl:41])[CH2:5][N:6]([CH3:20])[C:7]([C:9]1[CH2:10][N:11]([CH2:16][CH2:17][N:18]([CH3:19])[C:37]([NH2:36])=[O:38])[C:12](=[O:15])[C:13]=1[OH:14])=[O:8]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 54698194N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-[2-(methylamino)ethyl]-5-oxo-2H-pyrrole-3-carboxamide2×

Product 1

HCID 58699859HCID 58699859, compoundYield 61%

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) (153 mg, 0.374 mmol) in CH2Cl2 (5 mL) was added Et3N (0.14 mL, 1.0 mmol) followed by trimethylsilyl isocyanate (68 μL, 0.5 mmol) at room temperature. After 2 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 yield the title compound as a white powder (120 mg, 61% yield). 1HNMR (500 MHz, CDCl3) δ: 10.37 (1H, br s), 7.41 (1H, d, J=8.2H), 7.34 (1H, s), 7.10 (1H, d, J=8.2 Hz), 5.78 (2H, br s), 4.56 (2H, s), 4.22 (2H, s), 3.64 (2H, t, J=5.2 Hz), 3.55 (2H, t, J=5.2 Hz), 2.99 (3H, s), 2.94 (3H, s). HRMS calcd for C17H21Cl2N4O4 (M+H): 415.094. found: 415.0941.

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-911e228deafb47368790e008254e3b27
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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