1,2-Dichloroethane → HCID 59542929, compound

HRID 1876338Notes

Reaction equation

HRID 1876338 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH:27]([C:31](O)=[O:32])[CH2:26]3)[N:22]=1)=[CH:5]2.[CH3:34][NH:35][CH3:36].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:34][N:35]([CH3:36])[C:31]([CH:27]1[CH2:28][CH2:29][CH2:30][N:25]([CH2:24][CH2:23][C@@H:21]2[CH2:20][S:19][C:18]([C:6]3[NH:7][C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=4[NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:22]2)[CH2:26]1)=[O:32]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 59543036HCID 59543036, compound

Product 1

HCID 59542929HCID 59542929, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (84 mg, 0.18 mmol) prepared in Example 112 was dissolved in N,N-dimethylformamide (4 ml). Dimethylamine (0.13 ml, 2M in THF, 0.27 mmol), EDC (58 mg, 0.30 mmol) and HOBT (48 mg, 0.35 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, saturated sodium bicarbonate solution was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and concentrated. The residue was purified by column chromatography to give the title compound (18 mg, Yield 20%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0e6b23e8695d4d2daf99c68fc389161a
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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