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Sodium Carbonate → N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162432
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HRID 1162432 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=2)[N:7]=1.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:27]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:25][C:26]2[CH:31]=[C:30]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=4)[N:7]=3)[CH:29]=[CH:28][CH:27]=2)(=[O:24])=[O:23])=[CH:20][CH:21]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 162177213-(p-Toluenesulfonylamino)phenylboronic acid pinacol esterHCID 59519510N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide

생성물 1

HCID 44124523N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물
촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a 10-mL, round-bottomed flask was added N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide from Step 4 (0.060 g, 0.28 mmol), 4-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide (0.19 g, 0.51 mmol, Aldrich, St. Louis, Mo.), DMF (3.0 mL), and aq. sodium carbonate (0.85 mL, 1.7 mmol, 2 M). The mixture was carefully evacuated and backfilled with N2. Bis(triphenylphosphine)palladium(II) chloride (20 mg, 0.028 mmol, Strem Chemical, Inc., Newburyport, Mass.) was added. Once again, the mixture was carefully evacuated and backfilled with N2. The mixture was stirred at 100° C. for 2 h and then allowed to cool to room temperature. The mixture was poured into water (75 mL) and extracted with EtOAc (3×75 mL). The combined extracts were washed with water (2×50 mL) and brine (50 mL) then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as an off-white solid. MS (ESI positive ion) m/z: 422 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.92 (s, 1H), 10.44 (s, 1H), 8.26 (s, 1H), 8.05 (d, J=9.6 Hz, 1H), 7.77 (t, J=1.8 Hz, 1H), 7.67-7.71 (m, 3H), 7.61 (d, J=9.6 Hz, 1H), 7.40 (t, J=7.9 Hz, 1H), 7.35 (d, J=8.0 Hz, 2H), 7.19 (dd, J=8.0 Hz, 1.4 Hz, 1H), 2.32 (s, 3H), 2.11 (s, 3H).

후처리

  1. customThe mixture was carefully evacuated
  2. customOnce again, the mixture was carefully evacuated
  3. temperatureto cool to room temperature
  4. additionThe mixture was poured into water (75 mL)
  5. extractionextracted with EtOAc (3×75 mL)
  6. washThe combined extracts were washed with water (2×50 mL) and brine (50 mL)
  7. dry with materialthen dried (Na2SO4)
  8. concentrationconcentrated onto silica
  9. customPurification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2)

출처 및 근거

ORD 기록
ord-4c244a75a61245e09554f016448e7e4c
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07820665B2

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