Triethylamine → HCID 67274582, compound

HRID 1696726Notes

Reaction equation

HRID 1696726 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:22]1([O:28]C(Cl)=O)C=CC=CC=1.[NH2:32][C:33]1[N:38]=[C:37]([NH:39][C:40]([NH:42][CH3:43])=[O:41])[CH:36]=[C:35]([O:44][CH3:45])[CH:34]=1>C(#N)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9]([NH:12][C:22](=[O:28])[NH:32][C:33]3[CH:34]=[C:35]([O:44][CH3:45])[CH:36]=[C:37]([NH:39][C:40](=[O:41])[NH:42][CH3:43])[N:38]=3)(=[O:11])=[O:10])=[CH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 67274097HCID 67274097, compoundHCID 67274352HCID 67274352, compound

Product 1

HCID 67274582HCID 67274582, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5-chloro-benzo[b]thiophene-2-sulfonic acid amide (cf. Example 1a, 0.08 g, 0.32 mmol) in acetonitrile (3 mL) was added triethyamine (0.11 mL, 0.8 mmol) and, at 0-5° C., phenylchloroformate (0.061 g, 0.40 mmol). The mixture was stirred at rt for 2 h, and 1-(6-amino-4-methoxy-pyridin-2-yl)-3-methyl-urea (cf. Example 1b, 0.095 g, 0.52 mmol) was added. The reaction mixture was stirred at 55-60° C. for 3 h. After cooling to rt the solution was chromatographed directly over silica gel using dichloromethane/methanol as eluent. The compound containing fractions were evaporated. The crude compound was dissolved in a mixture of THF/methanol 1:1 (100 mL) and treated briefly with Amberlite IR-120 (H+). After filtration the filtrate was concentrated to obtain the title compound (0.066 g) as a colorless solid. MS (ISN): m/e 468.3, 470.1 (M−H)+

Workup

  1. customat 0-5° C.
  2. stirringThe reaction mixture was stirred at 55-60° C. for 3 h
  3. temperatureAfter cooling to rt the solution
  4. customwas chromatographed directly over silica gel
  5. additionThe compound containing fractions
  6. customwere evaporated
  7. dissolutionThe crude compound was dissolved in a mixture of THF/methanol 1:1 (100 mL)
  8. additiontreated briefly with Amberlite IR-120 (H+)
  9. filtrationAfter filtration the filtrate
  10. concentrationwas concentrated

Sources & evidence

ORD record
ord-fd741878aef84732a14a76028e41c229
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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