(2-(Methylthio)ethyl)amine → HCID 71262225, compound

HRID 540237Notes

Reaction equation

HRID 540237 reaction equation
[CH3:1]C(C)([O-])C.[Na+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15](OC(F)(F)F)[CH:16]=2)[N:11]=[C:10]([N:23]2[CH2:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[S:26](=[O:35])(=[O:34])[CH2:25][CH2:24]2)[CH:9]=1.[CH3:36][S:37][CH2:38][CH2:39][NH2:40]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:34]=[S:26]1(=[O:35])[C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[CH2:29][N:23]([C:10]2[CH:9]=[C:8]([NH:40][CH2:39][CH2:38][S:37][CH3:36])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:1])[CH:16]=3)[N:11]=2)[CH2:24][CH2:25]1

Participants

7

Reactant 3

HCID 87697(2-(Methylthio)ethyl)amineHCID 23676156Sodium t-butoxideHCID 712545694-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

Product 1

HCID 71262225HCID 71262225, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A dried microwave process vial capped with a rubber septum was purged with argon and charged with tris(dibenzylideneacetone)dipalladium(0) (2.88 mg, 0.005 mmol), 1-(N,N-dimethylamino)-1′-(dicyclohexylphosphino)biphenyl (5.90 mg, 0.015 mmol) and sodium tert-butoxide (134 mg, 1.4 mmol). The tube was purged with argon, and a solution of 4-(4-chloro-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (370 mg, 1.0 mmol, prepared in analogy to 4-(4-chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide in Example 17-1) and 2-(methylthio)ethylamine (128 mg, 1.4 mmol) in 1,4-dioxane (2.0 mL) was added. The mixture was heated with stirring in a sealed 5 mL of microwave process vial for 2 hour at 120° C. under microwave irradiation. After being cooled to room temperature, the reaction mixture was diluted with ethyl acetate, filtered through celite and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluting with 1-10% methanol in dichloromethane) to afford 341 mg of the desired product (yield was 80%). MS obsd. (ESI+) [(M+H)+] 428.

Workup

  1. customA dried microwave process vial capped with a rubber septum
  2. customwas purged with argon
  3. customThe tube was purged with argon
  4. temperatureThe mixture was heated
  5. temperatureAfter being cooled to room temperature
  6. filtrationfiltered through celite and
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluting with 1-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-bdf272642e3147448836dfac3b96ec72
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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