Potassium Carbonate → HCID 86662075, compound

HRID 1959385Notes

Reaction equation

HRID 1959385 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[C:23][Si](C)(C)C)=[N:20][C:19]([N:28]2[CH2:33][CH2:32][N:31]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])[CH2:30][CH2:29]2)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[C:11]([O:10][C:9]([N:8]([C:16]1[C:21]([C:22]#[CH:23])=[N:20][C:19]([N:28]2[CH2:33][CH2:32][N:31]([S:34]([CH2:37][CH3:38])(=[O:35])=[O:36])[CH2:30][CH2:29]2)=[CH:18][N:17]=1)[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:15])([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66745624Tert-butyl N-tert-butoxycarbonyl-5-(4-(ethylsulfonyl)piperazin-1-yl)-3-((trimethylsilyl)ethynyl)pyrazin-2-ylcarbamate

Product 1

HCID 86662075HCID 86662075, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tert-butyl N-tert-butoxycarbonyl-5-(4-(ethylsulfonyl)piperazin-1-yl)-3-((trimethylsilyl)ethynyl)pyrazin-2-ylcarbamate (589 mg, 1.037 mmol) was dissolved in anhydrous MeOH (10 mL) and treated with K2CO3 (14.33 mg, 0.1037 mmol). The reaction was allowed to stir at ambient temperature for 45 minutes. The solvent was removed in vacuo and the residue redissolved in DCM and washed with water followed by brine. The solution was dried (MgSO4), filtered and concentrated and the residue was purified by column chromatography (ISCO Companion™, 24 g column, 0-100% EtOAc/Petrol) to afford the title compound as an orange solid (287 mg, 60% Yield). 1H NMR (400.0 MHz, DMSO) d 1.23 (t, J=7.4 Hz, 3H), 1.38 (s, 18H), 3.11 (q, 2H), 3.26-3.34 (m, 4H), 3.69-3.71 (m, 4H), 4.65 (s, 1H) and 8.27 (s, 1H) ppm; MS (ES+) 396.0

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in DCM
  3. washwashed with water
  4. dry with materialThe solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography (ISCO Companion™, 24 g column, 0-100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-ab9dd39534cd4405b9d964f2a13e8192
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…