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

HRID 513679Notes

Reaction equation

HRID 513679 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[S:21](N)([NH2:24])(=[O:23])=[O:22].[H-].[H-].[H-].[H-].[Li+].[Al+3]>N1C=CC=CC=1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH:12]2[C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[N:10][CH:9]=[CH:8][CH:7]=4)[C:2]=3[NH:1][S:21](=[O:23])(=[O:22])[NH:24]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 82267SulfamideHCID 21226445Aluminium lithium hydrideHCID 68183219(8-Amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 681834241-(4-Fluoro-phenyl)-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 22%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(8-Amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone 367 (100 mg, 0.38 mmol) and sulfamide (361 mg, 3.76 mmol) in pyridine (3 ml) and were heated in a microwave at 140° C. for 2 h. After cooling, the mixture was concentrated in vacuo. The residue was dissolved in anhydrous THF (5 ml). LiAlH4 (26 mg, 0.75 mmol) was added and the mixture was stirred at room temperature for 18 h. The reaction was quenched with water (5 ml) and the resulting precipitate was collected by filtration and dried. The crude solid was purified by preparative HPLC (acidic conditions 1) to give the title compound (27 mg, 22%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in anhydrous THF (5 ml)
  4. customThe reaction was quenched with water (5 ml)
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried
  7. customThe crude solid was purified by preparative HPLC (acidic conditions 1)

Sources & evidence

ORD record
ord-a550b1e12e954f57a47c775c01b8348b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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