1,2-Dichloroethane → HCID 59543056, compound

HRID 1876330Notes

Reaction equation

HRID 1876330 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([O:25][CH3:26])[CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][C:22](O)=[O:23])[N:20]=2)=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:39][C:37]=2C=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([O:25][CH3:26])[CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][C:22]([NH:39][CH3:37])=[O:23])[N:20]=2)=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 25197164HCID 25197164, compound

Product 1

HCID 59543056HCID 59543056, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (83 mg, 0.22 mmol) prepared in Example 48 was dissolved in N,N-dimethylformamide (3 ml). Methylamine (0.17 ml, 2M in THF, 0.33 mmol), EDC (72 mg, 0.38 mmol) and HOBT (60 mg, 0.44 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 (39 mg, Yield 46%).

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-825c4f9590c14771a18dac54f3a24f03
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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