Triethylamine → HCID 68919991, compound

HRID 2104461Notes

Reaction equation

HRID 2104461 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7][NH:8][CH3:9])=[CH:5][S:4][C:3]=1[C:10]([NH:12][C@@H:13]1[CH2:18][C@@H:17]([C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:16][CH2:15][C@@H:14]1[NH:24][C:25](=[O:36])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=1)=[O:27])=[O:11].C(N(CC)CC)C.Br[CH2:45][CH2:46][N:47]=[C:48]=[O:49]>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[C:6]([CH2:7][N:8]([C:48]2[O:49][CH2:45][CH2:46][N:47]=2)[CH3:9])=[CH:5][S:4][C:3]=1[C:10]([NH:12][C@@H:13]1[CH2:18][C@@H:17]([C:19]([N:21]([CH3:22])[CH3:23])=[O:20])[CH2:16][CH2:15][C@@H:14]1[NH:24][C:25](=[O:36])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=1)=[O:27])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 42559572-Bromoethyl isocyanateHCID 57804528HCID 57804528, compound

Product 1

HCID 68919991HCID 68919991, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the compound obtained in Example 331 (590 mg) in methylene chloride (20 mL) were added triethylamine (0.735 mL) and 2-bromoethylisocyanate (0.106 mL), and the mixture was stirred for 18 hours at room temperature. The reaction mixture was diluted with methylene chloride, and the diluted solution was washed sequentially with water, 0.5N hydrochloric acid, water, saturated aqueous sodium bicarbonate, and saturated brine. The resultant organic layer was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The residue was purified through silica gel flash column chromatography (methylene chloride:methanol=20:1), and the solvent was removed under reduced pressure. The crude product was dissolved in methylene chloride (2 mL) and ethanol (3 mL), and 1N HCl in ethanol (0.5 mL) was added thereto, followed by stirring for 30 minutes at room temperature and concentration under reduced pressure. Diethyl ether was added to the residue, and the precipitated solid was collected through filtration and washed, to thereby yield the title compound (197 mg) as a colorless powder.

Workup

  1. washthe diluted solution was washed sequentially with water, 0.5N hydrochloric acid, water, saturated aqueous sodium bicarbonate, and saturated brine
  2. dry with materialThe resultant organic layer was dried over sodium sulfate anhydrate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through silica gel flash column chromatography (methylene chloride:methanol=20:1)
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe crude product was dissolved in methylene chloride (2 mL)
  7. additionethanol (3 mL), and 1N HCl in ethanol (0.5 mL) was added
  8. stirringby stirring for 30 minutes at room temperature
  9. concentrationconcentration under reduced pressure
  10. additionDiethyl ether was added to the residue
  11. filtrationthe precipitated solid was collected through filtration
  12. washwashed

Sources & evidence

ORD record
ord-4566c4a885434adead2db45d8d92b3bf
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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