Triethylamine → 1-Benzyl-5-chloro-3-chloromethylcinnolin-4(1H)-one

HRID 598157Notes

Reaction equation

HRID 598157 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH2:20]O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS([Cl:33])(=O)=O>ClCCl>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH2:20][Cl:33])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 672672091-Benzyl-5-chloro-3-hydroxymethylcinnolin-4(1H)-one

Product 1

HCID 672675101-Benzyl-5-chloro-3-chloromethylcinnolin-4(1H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.42 g (1.4 mmol) of 1-benzyl-5-chloro-3-hydroxymethylcinnolin-4(1H)-one in 25 mL of dichloromethane at 0° C. was added 0.97 mL (7.0 mmol) of triethylamine and 0.33 mL (4.2 mmol) of methanesulfonyl chloride. The reaction was allowed to warm to room temperature and stirred for 5 h. The reaction was concentrated by rotary evaporation and was subsequently dissolved in dichloromethane and concentrated onto silica gel. The crude material was purified by flash chromatography eluting with a 33-50% ethyl acetate/hexanes gradient mixture to give 0.26 g (59%) of the title compound as an off-white solid.

Workup

  1. concentrationThe reaction was concentrated by rotary evaporation
  2. dissolutionwas subsequently dissolved in dichloromethane
  3. concentrationconcentrated onto silica gel
  4. customThe crude material was purified by flash chromatography
  5. washeluting with a 33-50% ethyl acetate/hexanes gradient mixture

Sources & evidence

ORD record
ord-41e6e0f12f044669af05aab064d12633
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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