Triethylamine → HCID 42630608, compound

HRID 1696768Notes

Reaction equation

HRID 1696768 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:2]1.C(N(CC)CC)C.Cl[C:22](OC1C=CC=CC=1)=[O:23].[NH2:31][C:32]1[N:37]=[C:36]([NH:38][C:39]([NH:41][CH3:42])=[O:40])[CH:35]=[C:34]([S:43][CH3:44])[CH:33]=1>C(#N)C>[CH3:42][NH:41][C:39]([NH:38][C:36]1[N:37]=[C:32]([NH:31][C:22]([NH:13][S:10]([C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:1][CH:2]=2)(=[O:12])=[O:11])=[O:23])[CH:33]=[C:34]([S:43][CH3:44])[CH:35]=1)=[O:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 67273585HCID 67273585, compoundHCID 67274208HCID 67274208, compound

Product 1

HCID 42630608HCID 42630608, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

The above prepared benzofuran-3-sulfonic acid amide (0.050 g, 0.254 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with triethylamine (0.088 mL, 2.5 eq.) and phenyl chloroformate (0.0397 g, 1.0 eq.), and the mixture was then kept at ambient temperature for 1 h. 1-(6-Amino-4-methylsulfanyl-pyridin-2-yl)-3-methyl-urea (see below, 0.0538 g, 1.0 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, MeOH/AcOEt=5/95) and crystallization from AcOEt/heptane, delivered eventually 0.016 g of the title compound as off-white solid.

Workup

  1. dissolutionwas dissolved in 1.5 mL of abs
  2. additionwas then added
  3. temperatureCooling
  4. additionpouring
  5. extractionice, twofold extraction with AcOEt
  6. washwashing with water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  8. customfollowed by flash chromatography (SiO2, MeOH/AcOEt=5/95) and crystallization from AcOEt/heptane

Sources & evidence

ORD record
ord-f0c0f65ece53463da459bb58fc9da935
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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