3-Fluoroaniline → HCID 117771083, compound

HRID 2201575Notes

Reaction equation

HRID 2201575 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[F:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37]>CN(C=O)C.O.CCN(CC)CC>[NH2:1][C:2]1[C:3]([C:9]([NH:37][C:36]2[CH:38]=[CH:39][CH:40]=[C:34]([F:33])[CH:35]=2)=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 97423-FluoroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 117771083HCID 117771083, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3-amino-6-bromopyrazine-2-carboxylic acid (500 mg, 2.29 mmol), HOBT (464 mg, 3.44 mmol) and EDCI (660 mg, 3.44 mmol) were dissolved in dry DMF (20 mL), and the resulting solution was stirred for 6 hours. Then 3-fluoroaniline (305 mg, 2.75 mmol) and Et3N (0.43 mL) was added to the mixture. After being stirred overnight, the mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by prep-TLC (PE:EtOAc=6:1) to give the pure product of 3-amino-6-bromo-N-(3-fluorophenyl)pyrazine-2-carboxamide (500 mg, yield: 68%). 1H-NMR (CDCl3, 400 MHz) δ 9.44 (s, 1H), 8.22 (s, 1H), 7.59 (d, J=11.2 Hz, 1H), 7.24˜7.27 (m, 2H), 6.79˜6.82 (m, 1H), 3.21 (s, 2H). MS (M+H)+: 311/313.

Workup

  1. stirringAfter being stirred overnight
  2. extractionextracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by prep-TLC (PE:EtOAc=6:1)

Sources & evidence

ORD record
ord-078082da3f7549b99c5191096f823e1a
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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