Sodium hydride → HCID 117728141, compound

HRID 1772672Notes

Reaction equation

HRID 1772672 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH3:13])[C:7](=[O:12])[NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH3:13])[C:7](=[O:12])[N:8]([CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[S:9](=[O:10])(=[O:11])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 20755355HCID 20755355, compound

Product 1

HCID 117728141HCID 117728141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-bromo-4-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide (510 mg, 1.7 mmol) in DMF (10 mL), 60% NaH (69 mg, 1.7 mmol) was added in portions at 0° C. The resulting mixture was stirred at rt for 10 min and p-methoxybenzyl chloride (0.25 mL, 1.7 mmol) was added. The resulting mixture was stirred at 70° C. for 5 h, cooled to rt and poured over ice. The resulting compound was extracted with EtOAc (3×20 mL). The combined EtOAc layers were dried over Na2SO4, filtered, and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0-100% EtOAc/heptanes) to obtain compound 40a. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.01 (d, J=2.0 Hz, 1H), 7.74 (dd, J=8.8, 2.3 Hz, 1H), 7.40 (d, J=8.6 Hz, 2H), 7.10 (d, J=8.6 Hz, 1H), 6.83 (d, J=8.6 Hz, 2H), 4.99 (s, 2H), 3.77 (s, 3H).

Workup

  1. stirringThe resulting mixture was stirred at 70° C. for 5 h
  2. temperaturecooled to rt
  3. additionpoured over ice
  4. extractionThe resulting compound was extracted with EtOAc (3×20 mL)
  5. dry with materialThe combined EtOAc layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customwas purified by flash column chromatography on silica gel (0-100% EtOAc/heptanes)

Sources & evidence

ORD record
ord-785a4f6e6fa841af9aebe4258ef87b33
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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