Potassium Carbonate → HCID 90389190, compound

HRID 2203413Notes

Reaction equation

HRID 2203413 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[C:11](=[O:17])[N:10]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:9]=2)[CH:7]=1.[CH3:28][O:29][C:30]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:31]=1[CH2:32][N:33]([C:46]1[S:50][N:49]=[CH:48][N:47]=1)[S:34]([C:37]1[CH:42]=[C:41]([F:43])[C:40](F)=[CH:39][C:38]=1[F:45])(=[O:36])=[O:35].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][C:40]2[C:41]([F:43])=[CH:42][C:37]([S:34]([N:33]([CH2:32][C:31]3[CH:51]=[CH:52][C:53]([O:55][CH3:56])=[CH:54][C:30]=3[O:29][CH3:28])[C:46]3[S:50][N:49]=[CH:48][N:47]=3)(=[O:35])=[O:36])=[C:38]([F:45])[CH:39]=2)=[C:6]([C:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[C:11](=[O:17])[N:10]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:9]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 89544211HCID 89544211, compound

Product 1

HCID 90389190HCID 90389190, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(5-chloro-2-hydroxyphenyl)-7-(4-methoxybenzyl)imidazo[1,5-a]pyrazin-8(7H)-one (0.12 g, 0.31 mmol) and N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.15 g, 0.33 mmol) in dimethylsulfoxide (2 mL) was added potassium carbonate (0.051 g, 0.37 mmol). The reaction mixture was stirred at ambient temperature for 20 h and diluted with ethyl acetate (80 mL). The organic phase was washed with water (20 mL) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-80% gradient of ethyl acetate in hexanes to afford 4-(4-chloro-2-(7-(4-methoxybenzyl)-8-oxo-7,8-dihydroimidazo[1,5-a]pyrazin-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a colorless foam in 83% yield (0.203 g): 1H NMR (300 MHz, CDCl3) δ8.18 (s, 1H), 8.01 (s, 1H), 7.68 (s, 1H), 7.54-7.44 (m, 3H), 7.25-7.13 (m, 3H), 6.89-6.80 (m, 3H), 6.51 (dd, J=9.6, 6.1 Hz, 1H), 6.37 (s, 1H), 6.31 (dd, J=8.4, 2.1 Hz, 1H), 6.17 (d, J=2.1 Hz, 1H), 5.29 (s, 2H), 4.97 (s, 2H), 3.77 (s, 3H), 3.69 (s, 3H), 3.66 (s, 3H); MS (ES+) m/z 806.8 (M+1), 808.8 (M+1).

Workup

  1. washThe organic phase was washed with water (20 mL) and brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluting with a 20-80% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f3b9cc2c05a04382aa109b5166dac9dc
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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