2-Pyrazinecarboxylic acid → t-Butyl 2-(2-fluoro-4-((pyrazin-2-ylcarbonyl)amino)phenyl)pyrrolidine-1-carboxylate

HRID 13410Notes

Reaction equation

HRID 13410 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.Cl.CN(C)CCCN=C=NCC.N1C=CC=CC=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]2[CH2:39][CH2:38][CH2:37][N:36]2[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[C:31]([F:47])[CH:30]=1>C(Cl)(Cl)Cl>[F:47][C:31]1[CH:30]=[C:29]([NH:28][C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH:34]=[CH:33][C:32]=1[CH:35]1[CH2:39][CH2:38][CH2:37][N:36]1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]

Participants

6

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23145592t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate

Product 1

HCID 23145269t-Butyl 2-(2-fluoro-4-((pyrazin-2-ylcarbonyl)amino)phenyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.5 g of pyrazine-2-carboxylic acid and 3.1 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added to a pyridine (50 ml) solution of 3 g of t-butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate obtained in Example 338 (step 2), and the reaction liquid was stirred at room temperature for 3 hours. The reaction liquid was diluted with chloroform, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a yellow oily substance.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline in order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)
  7. customto obtain the entitled compound as a yellow oily substance

Sources & evidence

ORD record
ord-a9d1f97d113b42dda6ccf4e0de999b2f
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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