Hydrochloric Acid → HCID 46199403, compound

HRID 1959392Notes

Reaction equation

HRID 1959392 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:11]([NH:17]C(=O)OC(C)(C)C)=[N:12][CH:13]=[C:14](Br)[N:15]=1.[CH2:25]([S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28])[CH3:26].Cl.O1CCOCC1>COCCO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:11]([NH2:17])=[N:12][CH:13]=[C:14]([N:33]2[CH2:32][CH2:31][N:30]([S:27]([CH2:25][CH3:26])(=[O:28])=[O:29])[CH2:35][CH2:34]2)[N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 4152941-(Ethanesulfonyl)piperazineHCID 86662078HCID 86662078, compound

Product 1

HCID 46199403HCID 46199403, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of tert-butyl N-[3-(benzofuran-2-yl)-5-bromo-pyrazin-2-yl]carbamate, 1-ethylsulfonylpiperazine (164.5 mg, 0.9228 mmol) and 2-methoxyethanol (3 mL) were heated at 100° C. for 3 hours. The reaction mixture was allowed to cool to RT, treated with HCl in dioxane (384.5 μL of 4 M, 1.538 mmol) and allowed to stir at RT for 3 hours. The mixture was concentrated in vacuo and the resultant residue 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 and freeze-dried to give the title compound as an orange solid (15.5 mg, 12% Yield). 1H NMR (DMSO) d 1.24 (3H, t), 3.11 (2H, q), 3.45 masked signal, 3.51 (4H, m), 6.12 (2H, br s), 7.30 (1H, m), 7.34 (1H, m), 7.47 (1H, s), 7.71 (2H, m), 7.98 (1H, s) ppm; MS (ES+) 388.01

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resultant residue 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]
  3. customThe fractions were collected
  4. customfreeze-dried

Sources & evidence

ORD record
ord-8ff3fb761a5e4352a1751a072027a41f
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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