Ethanesulfonyl chloride → Tert-butyl N-tert-butoxycarbonyl-5-(4-(ethylsulfonyl)piperazin-1-yl)-3-((trimethylsilyl)ethynyl)pyrazin-2-ylcarbamate

HRID 1959384Notes

Reaction equation

HRID 1959384 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[C:7]([O:11][C:12]([N:14]([C:22]1[C:27]([C:28]#[C:29][Si:30]([CH3:33])([CH3:32])[CH3:31])=[N:26][C:25]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:24][N:23]=1)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:13])([CH3:10])([CH3:9])[CH3:8].CCN(C(C)C)C(C)C>CN(C=O)C>[C:7]([O:11][C:12]([N:14]([C:22]1[C:27]([C:28]#[C:29][Si:30]([CH3:31])([CH3:33])[CH3:32])=[N:26][C:25]([N:34]2[CH2:35][CH2:36][N:37]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:38][CH2:39]2)=[CH:24][N:23]=1)[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66744546HCID 66744546, compound

Product 1

HCID 66745624Tert-butyl N-tert-butoxycarbonyl-5-(4-(ethylsulfonyl)piperazin-1-yl)-3-((trimethylsilyl)ethynyl)pyrazin-2-ylcarbamateYield 109.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethanesulfonyl chloride (147.0 mg, 108.3 μL, 1.143 mmol) was added slowly to a stirred solution of tert-butyl N-tert-butoxycarbonyl-5-(piperazin-1-yl)-3-((trimethylsilyl)ethynyl)pyrazin-2-ylcarbamate (494 mg, 1.039 mmol) and DIPEA (161.2 mg, 217.3 μL, 1.247 mmol) in DMF (5 mL) at ambient temperature. The reaction was allowed to stir for 5 minutes and then partitioned between EtOAc/water. The aqueous layer was extracted with EtOAc (3×) and the combined organics washed with brine, dried (MgSO4), filtered and concentrated to give the product as a terracotta oil (645 mg, quantitative yield). MS (ES+) 590.05

Workup

  1. custompartitioned between EtOAc/water
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. washthe combined organics washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-666c29755a78445ca37d103c6af8676b
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…