Dimethyl Sulfoxide → HCID 66906099, compound

HRID 1691727Notes

Reaction equation

HRID 1691727 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)[CH3:22])[CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:32][C:33]1[C:34](Cl)=[N:35][CH:36]=[C:37]([CH:43]=1)[C:38]([O:40][CH2:41][CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[C:1]([O:5][C:6]([N:7]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:34]2[C:33]([Cl:32])=[CH:43][C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:36][N:35]=2)[CH2:11][CH:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)[CH3:22])=[O:31])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 16762519Ethyl 5,6-DichloronicotinateHCID 59178777HCID 59178777, compound

Product 1

HCID 66906099HCID 66906099, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 119 mg of the crude tert-butyl[(1R)-1-(3-methoxyphenyl)ethyl][(3-phenylpiperidin-4-yl)methyl]carbamate, 62 mg of ethyl 5,6-dichloronicotinate, and 39 mg of potassium carbonate was added 1.0 mL of DMSO at room temperature, and the mixed solution was stirred at 100° C. overnight. After cooling to room temperature, to the reaction mixture was added water, followed by extraction with ethyl acetate, and the organic layer was then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 132 mg of ethyl 6-[4-({(tert-butoxycarbonyl)[(1R)-1-(3-methoxyphenyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-5-chloronicotinate as a colorless foamy substance. FAB+: 608

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialthe organic layer was then dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1853c7b0370845d19ce288d16ff8d1ed
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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