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Dimethyl Sulfoxide → Diisopropyl Ether

HRID 1471798
Notes
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Reaction equation

HRID 1471798 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:12]=[C:13]3[CH:19]=[C:18]([CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[O:17][C:14]3=[CH:15][N:16]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].Cl[C:27]1[S:28][C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[CH:14]([O:17][CH:18]([CH3:20])[CH3:19])([CH3:15])[CH3:13].[CH3:1][S:2]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[CH:12]=[C:13]3[CH:19]=[C:18]([CH:20]4[CH2:25][CH2:24][N:23]([C:27]5[S:28][C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=5)[CH2:22][CH2:21]4)[O:17][C:14]3=[CH:15][N:16]=2)[CH2:9][CH2:10]1)(=[O:3])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 132467892-Chloro-5-trifluoromethyl-(1,3,4)thiadiazoleHCID 866945805-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-furo[2,3-c]pyridine

Product 2

HCID 7914Diisopropyl Ether
HCID 86694585
5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-[1-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperidin-4-yl]-furo[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-furo[2,3-c]pyridine (HCl salt, 70 mg), 2-chloro-5-trifluoromethyl-[1,3,4]thiadiazole (35 mg), K2CO3 (55 mg), and dimethyl sulfoxide (3 mL) is stirred at 60° C. overnight. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is triturated with methanol and then with diisopropylether to give the title compound. LC (method 1): tR=0.94 min; Mass spectrum (ESI+): m/z=514 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe resulting mixture is extracted with ethyl acetate
  3. washThe combined extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is triturated with methanol

Sources & evidence

ORD record
ord-ed1f1d48faa14d9886d38d67b650ab86
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012456B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes