Potassium Carbonate → HCID 66648304, compound

HRID 417943Notes

Reaction equation

HRID 417943 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:19](=[O:20])[CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16][C:14]=4[N:15]=3)[C:6]=2[CH:23]=1.Br[C:25]1[S:26][C:27]([CH3:30])=[N:28][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:22][C:17]1([CH3:21])[CH2:16][C:14]2[N:15]=[C:11]([N:7]3[C:6]4[CH:23]=[C:2]([O:1][C:25]5[S:26][C:27]([CH3:30])=[N:28][N:29]=5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)[S:12][C:13]=2[C:19](=[O:20])[CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 71719042-Bromo-5-methyl-1,3,4-thiadiazoleHCID 66648540HCID 66648540, compound

Product 1

HCID 66648304HCID 66648304, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 6 (75 mg, 0.23 mmol), 2-bromo-5-methyl-1,3,4-thiadiazole (42 mg, 0.23 mmol) and potassium carbonate (64 mg, 0.46 mmol) in DMF (7 mL) was heated to 150° C. for 10 h. The solvent was removed in vacuo and the residue was purified by prep HPLC to give the title compound (12 mg, 12%) as an off-white solid. δH (CDCl3) 1.14 (6H, s), 2.43 (2H, s), 2.67 (3H, s), 2.77 (2H, s), 4.09-4.15 (2H, m), 4.33-4.40 (2H, m), 6.96-7.06 (2H, m), 8.22-8.24 (1H, m). LCMS (ES+) 429 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-d442935d315c4546ba93647c99c94d36
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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