1,2-Dichloroethane → HCID 86659456, compound

HRID 246021Notes

Reaction equation

HRID 246021 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]2=[N:6][CH:7]=1.Cl.[NH2:23][C@@H:24]([CH3:30])[C:25]([CH3:29])([CH3:28])[C:26]#[N:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:26]([C:25]([CH3:29])([CH3:28])[C@@H:24]([NH:23][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[N:3]=2)[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=1)=[O:13])[CH3:30])#[N:27]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 584385252-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 866594481350712-71-8

Product 1

HCID 86659456HCID 86659456, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flask were combined 2-bromo-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1.10 g, 2.95 mmol), (S)-3-amino-2,2-dimethyl-butyronitrile hydrochloride (439 mg, 2.95 mmol), EDC (1.3 g, 6.8 mmol) and HOBt (1.15 g, 6.8 mmol). DMF (27 mL) was added followed by i-Pr2NEt (3.6 mL, 20.7 mmol). The reaction mixture was stirred at room temperature for 18 h and then quenched with water and extracted with EtOAc. The organics were washed with 10% citric acid, sat'd NaHCO3, sat'd LiCl, and sat'd NaCl then dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (50-100% EtOAc/hexane) to give 1.32 g (96%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-cyano-1,2,2-trimethyl-ethyl)-amide as an off-white powder.

Workup

  1. customIn a flask were combined
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe organics were washed with 10% citric acid
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 chromatography (50-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-0bd6223d5d4d40fb9684db4e20f3b6cf
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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