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

HRID 513663Notes

Reaction equation

HRID 513663 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[CH:10]=[CH:11][C:12]4[C:17](=[N:16][CH:15]=[CH:14][CH:13]=4)[C:8]=3[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 chloride2×HCID 68183219(8-Amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone2×

Product 1

HCID 681829551-(4-Fluoro-phenyl)-2-methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 14.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-Methylsulfamoyl chloride (Intermediate 213) (161 mg, 1.24 mmol) was added to suspension of (8-amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone (Intermediate 367) (110 mg, 0.41 mmol) in pyridine (10 ml) and the mixture was stirred room temperature for 18 h. NaBH4 (16 mg, 0.41 mmol) was added and the mixture was stirred at room temperature for a further 18 h. The reaction was quenched with 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 heptane/EtOAc (80:20-50:50 gradient) as the eluent to give the title compound (20 mg, 14%).

Workup

  1. stirringthe mixture was stirred at room temperature for a further 18 h
  2. customThe reaction was quenched with water (20 ml)
  3. extractionthe aqueous phase was extracted with EtOAc (30 ml)
  4. washThe organic phase was washed with brine (15 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated n vacuo
  7. customThe crude residue was purified by column chromatography heptane/EtOAc (80:20-50:50 gradient) as the eluent

Sources & evidence

ORD record
ord-b5e277b6f240476dacea8e8a95a7270d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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