1,2-Dichloroethane → HCID 59543067, compound

HRID 1876325Notes

Reaction equation

HRID 1876325 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][C:24](O)=[O:25])[N:22]=1)=[CH:5]2.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:39][C:37]=2C=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][C:24]([NH:39][CH3:37])=[O:25])[N:22]=1)=[CH:5]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 25196936HCID 25196936, compound

Product 1

HCID 59543067HCID 59543067, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (44 mg, 0.11 mmol) prepared in Example 31 was dissolved in N,N-dimethylformamide (2 ml). Methylamine (0.08 ml, 2M in THF, 0.17 mmol), EDC (36 mg, 0.19 mmol) and HOBT (30 mg, 0.22 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 37%).

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-23589b47f7494e649c6dc15152326d4f
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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