Triethylamine → HCID 86595899, compound

HRID 1373090Notes

Reaction equation

HRID 1373090 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:30])=[CH:16][C:17]([N:18]3[CH2:23][CH2:22][CH:21](O)[CH:20](C(OCC)=O)[CH2:19]3)=[C:12]2[C:11]([CH3:31])=[C:10]1[CH3:32].C(N([CH2:38][CH3:39])CC)C.CS(Cl)(=O)=[O:42].[C:45](=O)([O-])[OH:46].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:38]([O:42][C:20]1[CH2:19][N:18]([C:17]2[CH:16]=[C:15]([CH3:30])[N:14]=[C:13]3[N:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])[C:10]([CH3:32])=[C:11]([CH3:31])[C:12]=23)[C:23](=[C:45]=[O:46])[CH2:22][CH:21]=1)[CH3:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 121346591-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxypiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 86595899HCID 86595899, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (1.5 mL) were dissolved 1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxypiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (53 mg), triethylamine (34 mg) and a small amount of 4-dimethylaminopyridine. Methanesulfonyl chloride (25 mg) was added thereto and the resulting mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium hydrogencarbonate solution was poured into the reaction mixture, which was then extracted three times with chloroform. The combined organic layer was dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in benzene (1.0 mL), followed by adding thereto 1,8-diazabicyclo[5.4.0]-7-undecene (17 mg), and the resulting mixture was heated under reflux for 1 hour. A saturated aqueous ammonium chloride solution was poured into the reaction mixture, which was then extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, after which the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=5:1) to obtain 4-(5-ethoxy-carbonyl-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (27 mg).

Workup

  1. extractionwas then extracted three times with chloroform
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in benzene (1.0 mL)
  6. additionby adding
  7. temperature1,8-diazabicyclo[5.4.0]-7-undecene (17 mg), and the resulting mixture was heated
  8. temperatureunder reflux for 1 hour
  9. additionA saturated aqueous ammonium chloride solution was poured into the reaction mixture, which
  10. extractionwas then extracted three times with ethyl acetate
  11. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  12. filtrationafter which the desiccating agent was filtered off
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=5:1)

Sources & evidence

ORD record
ord-7882f2ae7e1e4f6ba49980c3cdd4604e
Source dataset
uspto-grants-2007_01
Patent number
US07160900B2

Reaction notes

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