Triethylamine → HCID 67422163, compound

HRID 1784224Notes

Reaction equation

HRID 1784224 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:16][CH:15]([CH2:17]O)[CH2:14]1)(=[O:12])=[O:11])([O-:3])=[O:2].CCN(CC)CC.S(Cl)(C)(=O)=O.CCN(C(C)C)C(C)C.[CH3:40][C:41]1[C:42]([CH:47]2[CH:52]([CH3:53])[CH2:51][CH2:50][CH:49]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=3)[NH:48]2)=[N:43][CH:44]=[CH:45][CH:46]=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH3:40][C:41]1[C:42]([CH:47]2[CH:52]([CH3:53])[CH2:51][CH2:50][CH:49]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=3)[N:48]2[CH2:17][CH:15]2[CH2:16][N:13]([S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH2:14]2)=[N:43][CH:44]=[CH:45][CH:46]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 65991607HCID 65991607, compoundHCID 67422809HCID 67422809, compound

Product 1

HCID 67422163HCID 67422163, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of [1-(2-nitro-benzenesulfonyl)-azetidin-3-yl]-methanol (165 mg, 0.606 mmol) in EtOAc (15 mL) was added Et3N (0.101 mL, 0.727 mmol) then mesyl chloride (0.052 mL, 0.666 mmol). The reaction mixture was stirred for 1 hour at room temperature. The precipitate was filtered through a plug of Celite and was washed with EtOAc. The filtrate was concentrated and the crude mesylate was dissolved in DMF (5 mL). To this solution was added DIPEA (0.211 mL, 1.20 mmol) and 3,3′-dimethyl-1′,2′,3′4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (162 mg, 0.606 mmol) and the mixture was heated at 80° C. for 17 hours. Saturated NaHCO3 (15 mL) was added and the mixture was extracted with CH2Cl2 (3×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by radial chromatography on silica gel (Et2O saturated with NH4OH) to give 3,3′-dimethyl-1′-[1-(2-nitro-benzenesulfonyl)-azetidin-3-ylmethyl]-1′,2′,3′4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (168 mg, 53%).

Workup

  1. filtrationThe precipitate was filtered through a plug of Celite
  2. washwas washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe crude mesylate was dissolved in DMF (5 mL)
  5. temperaturethe mixture was heated at 80° C. for 17 hours
  6. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by radial chromatography on silica gel (Et2O saturated with NH4OH)

Sources & evidence

ORD record
ord-95b95e90c71f45ecbbe9619ba59fb7a4
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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