Triethylamine → HCID 22024450, compound

HRID 1793095Notes

Reaction equation

HRID 1793095 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-193aa487bb724d47ad2b1c9bf3bf0bf9
Source dataset
uspto-grants-2006_07
Patent number
US07078405B2

Reaction notes

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