Ethanamine, 2-(ethylthio)- → N-{[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methyl}-2-(ethylsulfanyl)ethanamine

HRID 1882058Notes

Reaction equation

HRID 1882058 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28]([CH:31]=O)=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH2:33]([S:35][CH2:36][CH2:37][NH2:38])[CH3:34].C(=O)([O-])O.[Na+]>C(O)(=O)C.O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28]([CH2:31][NH:38][CH2:37][CH2:36][S:35][CH2:33][CH3:34])=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 148011Ethanamine, 2-(ethylthio)-HCID 516892Sodium BicarbonateHCID 593312942-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazole-5-carbaldehyde

Product 1

HCID 59331289N-{[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methyl}-2-(ethylsulfanyl)ethanamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazole-5-carbaldehyde (0.31 g), 2-(ethylsulfanyl)ethanamine (0.14 g), acetic acid (1 drop) and tetrahydrofuran (2 mL) was stirred overnight at 50° C. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was m washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was dissolved in methanol (4 mL), and sodium borohydride (28 mg) was added at 0° C. The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (0.37 g, quantitatively) was obtained as a yellow oil from a fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). MS: 471 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was m washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe obtained residue was dissolved in methanol (4 mL)
  6. additionsodium borohydride (28 mg) was added at 0° C
  7. stirringThe reaction mixture was stirred at room temperature for 1 hr
  8. additionwater was added
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-c68b1d6ad2d9472fa762f3e278eee141
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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