1,2-Dichloroethane → 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyanomethyl-amide

HRID 446939Notes

Reaction equation

HRID 446939 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(Cl)CCl.[NH2:28][CH2:29][C:30]#[N:31]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:29]([CH2:30][NH:31][C:13]([C:12]1[C:6]2[C:7](=[N:8][CH:9]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[N:5]=2)[N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[CH:11]=1)=[O:15])#[N:28]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 10901AminoacetonitrileHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 866576262-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyanomethyl-amideYield 88.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.20 g, 0.59 mmol) in CH2Cl2 (5 mL) was added EDC (0.14 g, 0.72 mmol), 4-(dimethylamino)pyridine (0.088 g, 0.72 mmol), and aminoacetonitrile (0.041 g, 0.72 mmol). The reaction mixture was stirred at room temperature for 5 h then diluted with CH2Cl2 and washed with H2O and brine. The organics were dried over Na2SO4 and concentrated. The residue was purified by SiO2 chromatography (25% EtOAc/hexanes) to obtain 0.194 g (88%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyanomethyl-amide a white solid.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organics were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by SiO2 chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2c3abe0e78824b8ab9dacf3f8fcdb8cf
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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