Hydrochloric Acid → HCID 178522103, compound

HRID 2223371Notes

Reaction equation

HRID 2223371 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C[Al](C)C.CCCCCC.[O:19]=[C:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]([NH:34][C:35]2[CH:39]=[CH:38][S:37][C:36]=2[C:40](OC)=[O:41])=[O:33])[CH2:28][CH2:27]1.Cl>C(Cl)(Cl)Cl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:40]([C:36]2[S:37][CH:38]=[CH:39][C:35]=2[NH:34][C:32]([C@H:29]2[CH2:28][CH2:27][C@H:26]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][C:20]3=[O:19])[CH2:31][CH2:30]2)=[O:33])=[O:41])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 661742-Amino-5-chloropyridineHCID 86584505Trimethylaluminum hexaneHCID 178499318HCID 178499318, compound

Product 1

HCID 178522103HCID 178522103, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Amino-5-chloropyridine (179 mg) is dissolved in chloroform (5 ml), and there to is added dropwise 0.98 M trimethyl aluminum-hexane solution (1.42 ml) under ice-cooling. The reaction solution is stirred at room temperature for 0.5 hours, and thereto is added methyl 3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)-thiophene-2-carboxylate (170 mg), and the mixture is heated to reflux for 18 hours. After allowing to cool, to the reaction mixture is added 10% hydrochloric acid (4 ml), and the mixture is extracted with chloroform. The organic layer is washed successively with water and saturated brine, dried over sodium sulfate, and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform) to give the title compound (172 mg). APCI-MS M/Z: 463/465[M+H]+

Workup

  1. temperaturecooling
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 18 hours
  4. temperatureto cool, to the reaction mixture
  5. extractionthe mixture is extracted with chloroform
  6. washThe organic layer is washed successively with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto remove the solvent under reduced pressure
  10. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-678ade35cc204f9fbf1ad97347efc27e
Source dataset
uspto-grants-2008_05
Patent number
US07375119B2

Reaction notes

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