Potassium Carbonate → HCID 71208754, compound

HRID 1622288Notes

Reaction equation

HRID 1622288 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:12]=[C:13]3[CH2:19][C@@:18]([CH3:26])([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:28]1[S:29][C:30]([C:33]([F:36])([F:35])[F:34])=[N:31][N:32]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][S:2]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[CH:12]=[C:13]3[CH2:19][C:18]([CH3:26])([CH:20]4[CH2:25][CH2:24][N:23]([C:28]5[S:29][C:30]([C:33]([F:36])([F:35])[F:34])=[N:31][N:32]=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]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 132467892-Chloro-5-trifluoromethyl-(1,3,4)thiadiazoleHCID 67973724HCID 67973724, compound

Product 1

HCID 71208754HCID 71208754, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound is prepared from (S)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-methyl-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine (Intermediate 41; the configuration of the stereocenter is arbitrarily assigned) and 2-chloro-5-trifluoromethyl-[1,3,4]thiadiazole in dimethylsulfoxide at 85° C. in the presence of potassium carbonate. LC (method 4): tR=0.98 min; Mass spectrum (ESI+): m/z=530 [M+H]+.

Workup

  1. customat 85° C.

Sources & evidence

ORD record
ord-1809a94e4a0f4b28be4eab03fe0d1997
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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