1,2-Dichloroethane → HCID 44187344, compound

HRID 1802814Notes

Reaction equation

HRID 1802814 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:5]2.[N:27]1([CH2:33][CH2:34][NH2:35])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl-].[Na+]>CN(C)C=O>[N:27]1([CH2:33][CH2:34][NH:35][C:18]([CH:15]2[CH2:16][CH2:17][CH:12]([NH:11][C:9]3[CH:10]=[C:2]([CH3:1])[CH:3]=[C:4]4[C:8]=3[NH:7][C:6]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:5]4)[CH2:13][CH2:14]2)=[O:20])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 5234Sodium ChlorideHCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 44187345HCID 44187345, compound

Product 1

HCID 44187344HCID 44187344, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound obtained in Example 55 (30 mg, 0.09 mmol) was dissolved in N,N-dimethyl formamide 5 ml. 2-Morpholine-4-yl-ethylamine (22 mg, 0.17 mmol), EDC (25 mg, 0.19 mmol) and HOBT (18 mg, 0.19 mmol) were added. The mixture was stirred for 8 hours at room temperature. Saturated 1N aqueous sodium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to give the title compound 40 mg (Yield 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationThe filtrate was distilled under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-ace989a636914a308ded1b3e639d722e
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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