1,2-Dichloroethane → HCID 67388110, compound

HRID 446932Notes

Reaction equation

HRID 446932 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([NH:15][CH:16]([CH3:21])[CH2:17][C:18](O)=[O:19])=[O:14])=[CH:11][N:10]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(Cl)CCl.Cl.[CH2:35]([NH2:37])[CH3:36]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[CH2:35]([NH:37][C:18]([CH2:17][CH:16]([NH:15][C:13]([C:12]1[C:6]2[C:7](=[N:8][CH:9]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[N:5]=2)[N:10]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[CH:11]=1)=[O:14])[CH3:21])=[O:19])[CH3:36]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 11198Ethylamine hydrochlorideHCID 58436623HCID 58436623, compound

Product 1

HCID 67388110HCID 67388110, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{[2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-butyric acid (0.14 g, 0.33 mmol) in CH2Cl2 (5 mL) was added EDC (0.083 g, 0.43 mmol), 4-(dimethylamino)pyridine (0.053 g, 0.43 mmol), and ethylamine hydrochloride (0.035 g, 0.43 mmol). The reaction mixture was stirred at room temperature overnight then diluted with H2O and extracted with CH2Cl2. The combined organics were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by SiO2 chromatography (2% MeOH/CH2Cl2) to obtain 0.114 g (78%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-ethylcarbamoyl-1-methyl-ethyl)-amide as an oil.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2d52bbdef73c4d49869f45df84870528
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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