Ammonium Chloride → HCID 59375562, 화합물

HRID 2193013노트

반응식

HRID 2193013 반응식
[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

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium Hexamethyldisilazide2회HCID 14002850methyl 2-(N-methyl-N-phenylsulfamoyl)acetateHCID 59375369HCID 59375369, 화합물

생성물 1

HCID 59375562HCID 59375562, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-48c4406302af4463a4900dad2d6103f1
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329722B2

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