Triethylamine → 6-(phenylsulfonamido)-N-(tetrahydro-2H-pyran-2-yloxy)quinoline-3-carboxamide

HRID 1894964Notes

Reaction equation

HRID 1894964 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21](O)=[O:22])=[CH:14]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.CN(C)C(F)=[N+](C)C.[O:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH:47]1[O:52][NH2:53]>CN(C)C=O.O>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([NH:53][O:52][CH:47]2[CH2:48][CH2:49][CH2:50][CH2:51][O:46]2)=[O:22])=[CH:14]3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 670023616-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid

Product 1

HCID 866595026-(phenylsulfonamido)-N-(tetrahydro-2H-pyran-2-yloxy)quinoline-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid (0.11 g, 0.335 mmol) was dissolved in N,N-dimethylformamide (2.5 mL) and triethylamine (0.14 mL, 1 mmol) was added. Tetramethylfluoroformamidinium hexafluorophosphate (0.106 g, 0.402 mmol) was added and the reaction mixture was allowed to stir at room temperature for 15 min. Then O-(tetrahydropyran-2-yl)hydroxylamine (0.0471 g, 0.402 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate three times. The combined extracts were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-10% MeOH in methylene chloride gradient with 0.1% formic acid) to afford the product (Int-13, 0.027 g, 18%). LC-MS: (AA) ES+ 428.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate three times
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica gel chromatography (0-10% MeOH in methylene chloride gradient with 0.1% formic acid)
  8. customto afford the product (Int-13, 0.027 g, 18%)

Sources & evidence

ORD record
ord-834e8e84bc044ce78d4d1dae591de334
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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