Triethylamine → HCID 59680249, compound

HRID 419923Notes

Reaction equation

HRID 419923 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]2[N:16]([CH:17]=1)[C:15]([CH2:18]O)=[CH:14][S:13]2)([O-:3])=[O:2].[CH2:20]([N:22](CC)[CH2:23][CH3:24])[CH3:21].CS(Cl)(=O)=O.N1CCCC1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]2[N:16]([CH:17]=1)[C:15]([CH2:18][N:22]1[CH2:23][CH2:24][CH2:21][CH2:20]1)=[CH:14][S:13]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 25232523[6-(2-Nitrophenyl)imidazo[2,1-b][1,3]thiazol-3-yl]methanol

Product 1

HCID 59680249HCID 59680249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[6-(2-Nitro-phenyl)-imidazo[2,1-b]thiazol-3-yl]-methanol (110 mg, 0.4 mmol) in CH2Cl2 (5 ml) with triethylamine (56 ul, 1 eq) was cooled to 0° C. Methylsulfonyl chloride (31 ul, 1 eq) was added dropwise, stirred at 0° C. for 10 min, warmed to room temperature, and stirred for 15 min. The reaction was quenched by the addition of brine, and the mesylate was extracted with CH2Cl2, dried over Na2SO4 and concentrated. The residue was dissolved in acetonitrile (3 ml), and added triethylamine (31 ul, 1 eq), followed by pyrrolidine (66 ul, 2 eq). The reaction mixture was stirred for 2 hours, concentrated and chased with pentane. Column chromatography in CH2Cl2 (0 to 4% MeOH gradient) gave 6-(2-Nitro-phenyl)-3-pyrrolidin-1-ylmethyl-imidazo[2,1-b]thiazole. This material was dissolved in methanol (16 ml) and a solution of sodium hydrogen sulfide (112 mg, 5 eq) in water (4 ml) was added. The reaction mixture was refluxed for 2 days with additional charges of NaHS (2×112 mg). The reaction was concentrated to remove the methanol, and the aqueous solution was extracted with CH2Cl2 (3×40 ml). The organic layer was dried over Na2SO4, and concentrated to obtain the product as a yellow film, 109 mg. (MS, M++H=299.1)

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 15 min
  3. customThe reaction was quenched by the addition of brine
  4. extractionthe mesylate was extracted with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in acetonitrile (3 ml)
  8. stirringThe reaction mixture was stirred for 2 hours
  9. concentrationconcentrated and chased with pentane

Sources & evidence

ORD record
ord-3a6152f4a65d4479b0fe572efc5c7d55
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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