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1,4-Dioxane → HCID 57970213, compound

HRID 1666633
Notes
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Reaction equation

HRID 1666633 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1.Cl.[NH2:13][C@H:14]1[CH2:18][CH2:17][N:16]([C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)[CH2:15]1.O1CCOCC1.CC(C)([O-])C.[Na+]>C(OCC)(=O)C.O.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]>[CH3:11][C:4]1[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=[C:2]([NH:13][C@H:14]2[CH2:18][CH2:17][N:16]([C:19](=[O:32])[CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:25][CH:26]=3)[CH2:15]2)[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 23676156Sodium t-butoxideHCID 552633012-Chloro-4-methylthieno[3,4-B]pyridineHCID 86636479(S)-1-(3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride

Product 1

HCID 57970213HCID 57970213, compoundYield 26.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-chloro-4-methylthieno[3,4-b]pyridine (0.022 g), Pd2(dba)3 (0.005 g), (±)-BINAP (0.011 g), 1-((S)-3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride (0.046 g), and 1,4-dioxane (0.5 mL) was added sodium t-butoxide (0.045 g) under nitrogen atmosphere, and the mixture was stirred at 70° C. for 30 min. The reaction mixture was diluted with ethyl acetate and water, then the interlayer was removed by Celite filtration, and the organic layer was washed with saturated brine. The organic layer was dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/methanol=20:1, and silica gel, chloroform/methanol=20:1) to obtain light yellow oily (S)-1-(3-(4-methylthieno[3,4-b]pyridin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (0.014 g).

Workup

  1. customthe interlayer was removed by Celite filtration
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/methanol=20:1, and silica gel, chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-f60673dc5a1f46ba859a7bdeef590394
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044068B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes