Hydrochloric Acid → HCID 178440499, 화합물

HRID 1693683노트

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HRID 1693683 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28]([C:32]#[N:33])=[CH:27][CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:34]([CH3:36])[CH3:35])[O:11][N:10]=1.[Cl-].[NH4+].[N-:39]=[N+:40]=[N-:41].[Na+].Cl>CN(C)C=O.O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28]([C:32]3[NH:41][N:40]=[N:39][N:33]=3)=[CH:27][CH:26]=[CH:25]4)=[CH:20][CH:21]=2)=[C:12]([CH:34]([CH3:36])[CH3:35])[O:11][N:10]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 247393306-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarbonitrile

생성물 1

HCID 178440499HCID 178440499, 화합물수율 79.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarbonitrile (75 mg, 0.14 mmol) in dimethylformamide (1 mL) was added ammonium chloride (8.5 mg, 0.15 mmol) and sodium azide (10 mg, 0.15 mmol). The mixture was then heated to 100° C. for 18 hours. The reaction was diluted with water (5 mL) and acidified with 2 N HCl (2 mL). A white precipitate was formed upon acidification which was removed via filtration and dried under high vacuum for four hours. The crude residue was then dissolved in methanol (5 mL) and purified via preparative high pressure liquid chromatography (C18 Luna column eluted with a 10-100% gradient of acetonitrile in water with 0.1% formic acid modifier) to give the title compound as a white solid (62 mg, 78%) 1H NMR (CDCl3): 8.54 (d, J=9 Hz, 1H), 7.91-8.02 (m, 2H), 7.75 (d, J=9 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 7.54 (dd, J=2, 8 Hz, 1H), 7.60-7.48 (m, 3H) 7.38 (d, J=9 Hz, 2H), 7.34-7.27 (m, 1H), 6.88 (d, J=9 Hz, 2H), 4.78 (s, 2H), 3.42-3.28 (m, 1H), 1.53-1.34 (m, 6H). ESI-LCMS m/z 556 (M+H)+.

후처리

  1. customA white precipitate was formed upon acidification which
  2. customwas removed via filtration
  3. customdried under high vacuum for four hours
  4. dissolutionThe crude residue was then dissolved in methanol (5 mL)
  5. custompurified via preparative high pressure liquid chromatography (C18 Luna column
  6. washeluted with a 10-100% gradient of acetonitrile in water with 0.1% formic acid modifier)

출처 및 근거

ORD 기록
ord-b2b0d21ea31d4e28b78d8495a2d62173
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158665B2

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