Ammonium Chloride → HCID 59375562, compound

HRID 2193013Notes

Reaction equation

HRID 2193013 reaction equation
[CH3:1][N:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[S:3]([CH2:6][C:7](OC)=O)(=[O:5])=[O:4].[Cl:17][C:18]1[N:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[C:20]1[CH:32]=[N:31][CH:30]=[CH:29][C:21]=1C(Cl)=[N:23]2.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Cl:17][C:18]1[N:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[C:20]1[CH:32]=[N:31][CH:30]=[CH:29][C:21]=1[C:7]([CH2:6][S:3]([N:2]([CH3:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:5])=[O:4])=[N:23]2

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium Hexamethyldisilazide2×HCID 14002850HCID 14002850, compoundHCID 59375369HCID 59375369, compound

Product 1

HCID 59375562HCID 59375562, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of methyl {[methyl(phenyl)amino]sulfonyl}acetate (1021 mg, 4.20 mmol) and 1,6-dichloropyrido[4,3-c]-1,6-naphthyridine (350 mg, 1.400 mmol) in toluene (14.0 mL) at 0° C., LHMDS (4.20 mL, 4.20 mmol, 1 M in THF) was added dropwise. The reaction was allowed to warm to room temperature and was stirred for 5 h. The reaction mixture was then heated to 50° C. for 1 h. The reaction mixture was then stirred at room temperature for 72 h. To the reaction mixture, LHMDS (1.400 mL, 1.400 mmol, 1 M in THF) was added, and the reaction was stirred at room temperature overnight. This mixture was poured into aqueous ammonium chloride (saturated). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were filtered through a frit, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexanes, to afford 1-(1-chloropyrido[4,3-c]-1,6-naphthyridin-6-yl)-N-methyl-N-phenylmethanesulfonamide as a brown solid. LRMS (APCI) calc'd for (C19H16ClN4O2S) [M+H]+, 399.1; found 399.0.

Workup

  1. temperatureThe reaction mixture was then heated to 50° C. for 1 h
  2. stirringThe reaction mixture was then stirred at room temperature for 72 h
  3. stirringthe reaction was stirred at room temperature overnight
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. filtrationThe combined organic extracts were filtered through a frit
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-48c4406302af4463a4900dad2d6103f1
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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