1,2-Dichloroethane → HCID 86657869, compound

HRID 1898497Notes

Reaction equation

HRID 1898497 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]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:33][C:32]([CH3:35])([CH3:34])[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])[C:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57516598(R)-2-amino-3,3-dimethyl-1-(pyrrolidin-1-yl)butan-1-one hydrochlorideHCID 584385252-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 86657869HCID 86657869, compoundYield 90%

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 (125 mg, 0.34 mmol), (R)-2-amino-3,3-dimethyl-1-pyrrolidin-1-yl-butan-1-one hydrochloride (155 mg, 0.70 mmol), EDC (148 mg, 0.77 mmol) and HOBt (104 mg, 0.772 mmol). DMF (4.0 mL) was added followed by i-Pr2NEt (0.19 mL, 1.07 mmol). The reaction mixture was stirred at room temperature for 1 h and then concentrated. The residue was taken up in EtOAc and 10% citric acid and the organic layer washed with 10% citric acid, sat. NaHCO3, sat LiCl and brine, dried over MgSO4, and concentrated to give 162 mg (90%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a viscous brown oil.

Workup

  1. customIn a flask were combined
  2. concentrationconcentrated
  3. wash10% citric acid and the organic layer washed with 10% citric acid, sat. NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94523440a10d4a5b8d4aa48d0486decd
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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