2-Pyrazinecarboxylic acid → HCID 60205352, compound

HRID 408211Notes

Reaction equation

HRID 408211 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[C:19](O)=[O:20].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.[Li+].[OH-]>C(Cl)Cl.O>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:19]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][N:13]=3)=[O:20])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205352HCID 60205352, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.200 g, 0.869 mmol, Example 1, Step H), pyrazine-2-carboxylic acid (0.227 g, 1.83 mmol), BOP-Cl (0.465 g, 1.83 mmol), and triethylamine (0.606 ml, 4.35 mmol) were placed in DCM (5 mL) and stirred at room temperature for 30 minutes. 3M LiOH (3 mL) was then added, and the reaction was stirred for an additional 10 minutes and then poured into water. The mixture was then filtered, washed with DCM, and then washed with 10:1 DCM:MeOH and dried to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazine-2-carboxamide (0.180 g, 61% yield) as a solid.

Workup

  1. stirringthe reaction was stirred for an additional 10 minutes
  2. filtrationThe mixture was then filtered
  3. washwashed with DCM
  4. washwashed with 10:1 DCM
  5. dry with materialMeOH and dried

Sources & evidence

ORD record
ord-23af6404519e413088e4212c593415f9
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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