Ethyl Acetate → HCID 178477705, compound

HRID 1959375Notes

Reaction equation

HRID 1959375 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10]([C:13]3[C:14]([NH2:20])=[N:15][CH:16]=[C:17](Br)[N:18]=3)=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:21]([S:23]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)(=[O:25])=[O:24])[CH3:22].CCOC(C)=O>O>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10]([C:13]3[C:14]([NH2:20])=[N:15][CH:16]=[C:17]([N:29]4[CH2:28][CH2:27][N:26]([S:23]([CH2:21][CH3:22])(=[O:24])=[O:25])[CH2:31][CH2:30]4)[N:18]=3)=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4152941-(Ethanesulfonyl)piperazineHCID 178507534HCID 178507534, compound

Product 1

HCID 178477705HCID 178477705, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[5-(3-aminophenyl)-4H-1,2,4-triazol-3-yl]-5-bromo-pyrazin-2-amine (220 mg, 0.6623 mmol) was heated in neat 1-ethanesulfonyl piperazine (590.4 mg, 3.312 mmol) in the microwave at 190° C. for 2 hours. The reaction was treated with EtOAc and H2O, the two layers separated and the organics dried and concentrated to give a yellow oil which was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a yellow solid (23.9 mg, 8% Yield). 1H NMR (400.0 MHz, DMSO) d 8.38 (s, 2H), 8.04 (s, 1H), 7.33 (s, 2H), 7.24 (s, 1H), 7.09 (s, 1H), 6.96 (s, 1H), 6.60 (s, 1H), 3.55 (s, 4H), 3.28 (s, 4H), 3.08 (d, J=5.7 Hz, 2H) and 1.20 (s, 3H) ppm; MS (ES+) 430.0

Workup

  1. customthe two layers separated
  2. customthe organics dried
  3. concentrationconcentrated
  4. customto give a yellow oil which
  5. customwas purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  6. customThe fractions were collected
  7. customfreeze-dried

Sources & evidence

ORD record
ord-1cad82d59a1b4cc89725be48e81ed5de
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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