Hydrochloric Acid → HCID 88861907, compound

HRID 513699Notes

Reaction equation

HRID 513699 reaction equation
Cl.[O:2]1CCO[CH:3]1[C:7]1[CH:8]=[C:9]([CH:14]2[C:27]3[CH:26]=[CH:25][C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[C:18]=3[NH:17][S:16](=[O:29])(=[O:28])[N:15]2[CH3:30])[CH:10]=[CH:11][C:12]=1[F:13].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[F:13][C:12]1[CH:11]=[CH:10][C:9]([CH:14]2[C:27]3[CH:26]=[CH:25][C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[C:18]=3[NH:17][S:16](=[O:29])(=[O:28])[N:15]2[CH3:30])=[CH:8][C:7]=1[CH:3]=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 68183345HCID 68183345, compound

Product 1

HCID 88861907HCID 88861907, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

6 M HCl (5 ml) was added dropwise to a solution of 1-(3-[1,3]dioxolan-2-yl-4-fluoro-phenyl)-2-methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide 421 (390 mg, 0.94 mmol) in THF (10 ml) and the mixture was heated at 70° C. for 3 h. After cooling, the mixture was neutralised with sat K2CO3 and the aqueous phase was extracted with EtOAc (30 ml). The organic phase was washed with brine (10 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (95:5) as the eluent to give the title compound (180 mg, 52%).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with EtOAc (30 ml)
  3. washThe organic phase was washed with brine (10 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with DCM/MeOH (95:5) as the eluent

Sources & evidence

ORD record
ord-5aa6d60435ed43468ad7749e5c6ff49b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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