Sodium borohydride → 1-(4-Fluoro-phenyl)-2-methyl-1,4,5,6,7,8-hexahydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide

HRID 513678Notes

Reaction equation

HRID 513678 reaction equation
[CH3:1][NH:2][S:3](Cl)(=[O:5])=[O:4].[NH2:7][C:8]1[C:9]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=O)=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2.[BH4-].[Na+]>N1C=CC=CC=1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH:18]2[C:9]3[C:8](=[C:17]4[C:12](=[CH:11][CH:10]=3)[CH2:13][CH2:14][CH2:15][NH:16]4)[NH:7][S:3](=[O:5])(=[O:4])[N:2]2[CH3:1])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chlorideHCID 68183219(8-Amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 681834321-(4-Fluoro-phenyl)-2-methyl-1,4,5,6,7,8-hexahydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-methylsulfamoyl chloride 213 (729.9 mg, 5.63 mmol) was added to a solution of (8-amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone 367 (500 mg, 1.88 mmol) in pyridine (20 ml) and the mixture was stirred at room temperature for 18 h. NaBH4 (213 mg, 5.63 mmol) was added and stirring was continued at room temperature for 16 h. The reaction was quenched by the addition of water (20 ml) and the aqueous phase was extracted with EtOAc (30 ml). The organic phase was washed with brine (15 ml), dried (Na2SO4) and concentrated n vacuo. The crude residue was purified by column chromatography with heptane/EtOAc as the eluent to give the title compound (12 mg, 2%).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 16 h
  3. customThe reaction was quenched by the addition of water (20 ml)
  4. extractionthe aqueous phase was extracted with EtOAc (30 ml)
  5. washThe organic phase was washed with brine (15 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated n vacuo
  8. customThe crude residue was purified by column chromatography with heptane/EtOAc as the eluent

Sources & evidence

ORD record
ord-9f1118930d7e4c528c4e85c3480d46cc
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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