Potassium Carbonate → HCID 90397726, compound

HRID 2203422Notes

Reaction equation

HRID 2203422 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]=2[CH:25]=1.[CH3:26][O:27][C:28]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:29]=1[CH2:30][N:31]([C:44]1[S:48][N:47]=[CH:46][N:45]=1)[S:32]([C:35]1[CH:40]=[C:39]([F:41])[C:38](F)=[CH:37][C:36]=1[F:43])(=[O:34])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[CH3:26][O:27][C:28]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:29]=1[CH2:30][N:31]([C:44]1[S:48][N:47]=[CH:46][N:45]=1)[S:32]([C:35]1[C:36]([F:43])=[CH:37][C:38]([O:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][N:8]=[C:7]([N:10]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:6]=3[CH:25]=2)=[C:39]([F:41])[CH:40]=1)(=[O:34])=[O:33]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 89555370HCID 89555370, compound

Product 1

HCID 90397726HCID 90397726, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of di-tert-butyl (5-hydroxy-1,2-benzoxazol-3-yl)imidodicarbonate (0.40 g, 1.1 mmol) in dimethyl sulfoxide (5 mL) was added N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.50 g, 1.1 mmol) and potassium carbonate (0.19 g, 1.4 mmol). The reaction was stirred at ambient temperature for 18 h, diluted with ethyl acetate (10 mL), washed with water (3×10 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford di-tert-butyl (5-{4-[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)sulfamoyl]-2,5-difluorophenoxy}-1,2-benzoxazol-3-yl)imidodicarbonate as a colorless solid in 87% yield (1.09 g): 1H NMR (300 MHz, CDCl3) δ8.17 (s, 1H), 7.66-7.59 (m, 2H), 7.30-7.26 (m, 2H), 7.18-7.16 (m, 1H), 6.45-6.40 (m, 1H), 6.35 (d, J=8.1 Hz, 1H), 6.37 (s, 1H), 2.60 (s, 2H), 3.75 (s, 3H), 3.70 (s, 3H), 1.56 (s, 9H), 1.40 (s, 9H); MS (ES+) m/z 775.8 (M+1).

Workup

  1. washwashed with water (3×10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe79b38eee214f46af8d81ccaea635cd
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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