Triethylamine → HCID 22024450, compound

HRID 501020Notes

Reaction equation

HRID 501020 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[O:19][CH3:20])=[N:9][CH:8]=[CH:7][N:6]2[C:21]=1[C:22](O)([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:20][O:19][C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:10]1[C:5]2[N:6]([C:21](/[C:22](/[CH2:26][CH2:27][CH3:28])=[CH:23]\[CH2:24][CH3:25])=[C:3]([CH2:1][CH3:2])[N:4]=2)[CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22024588HCID 22024588, compound

Product 1

HCID 22024450HCID 22024450, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-Ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-4-heptanol (115 mg, 0.29 mmol) and triethylamine (0.48 mL, 3.5 mmol) were dissolved in methylene chloride (3 mL), then methanesulfonyl chloride (0.13 mL, 1.7 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temperature for 1 hour. An aqueous saturated sodium bicarbonate solution was added to the reaction mixture, which was extracted with ethyl acetate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) to give the title compound (111 mg) as a colorless oil.

Workup

  1. temperatureunder ice-cooling
  2. extractionwas extracted with ethyl acetate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-347febe713324ae087838292c869d5f7
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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