Acetyl chloride → HCID 118079610, compound

HRID 1485734Notes

Reaction equation

HRID 1485734 reaction equation
C(N(CC)C(C)C)(C)C.[Br:10][C:11]1[N:31]=[CH:30][C:14]2[NH:15][C@@H:16]([CH3:29])[CH2:17][N:18]([S:19]([C:22]3[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=1.[C:32](Cl)(=[O:34])[CH3:33]>ClCCl>[Br:10][C:11]1[N:31]=[CH:30][C:14]2[N:15]([C:32](=[O:34])[CH3:33])[C@@H:16]([CH3:29])[CH2:17][N:18]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 118079038HCID 118079038, compound

Product 1

HCID 118079610HCID 118079610, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (0.018 mL, 0.102 mmol) was added to a solution of (S)-7-bromo-3-methyl-1-tosyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine (0.013 g, 0.034 mmol) and acetyl chloride (3.6 μL, 0.051 mmol) in dichloromethane (2.0 mL), and the mixture stirred at room temperature for 2 h. The reaction mixture was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a yellow oil. This material was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 50-100% ethyl acetate-hexane) to afford (S)-1-(7-bromo-3-methyl-1-tosyl-2,3-dihydropyrido[3,4-b]pyrazin-4(1H)-yl)ethanone (0.010 g, 69%) as an off-white solid. MS (ESI, pos. ion) m/z 424, 426.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. customThe aqueous phase was separated
  3. extractionextracted with dichloromethane
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil
  9. customThis material was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 50-100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-98dfda2566b04a9eaa176eed1c024e7c
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

Loading…