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Hydrochloric Acid → 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4,4]nonan-1-yl)-2-fluoro-N-methylbenzamide

HRID 240815
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HRID 240815 반응식
[CH3:1][NH:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2([C:16]#N)[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][C:5]=1[F:18].[N:20]([C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=1)=[C:21]=[S:22].C[OH:36].Cl>CN(C=O)C.O>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([N:20]2[C:16](=[O:36])[C:11]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[N:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([NH:2][CH3:1])=[O:19])=[C:5]([F:18])[CH:6]=3)[C:21]2=[S:22])=[CH:24][C:25]=1[C:31]([F:32])([F:34])[F:33])#[N:28]
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7

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HCID 313Hydrochloric AcidHCID 887MethanolHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 59296600N-Methyl 2-fluoro-4-(1-cyanocyclopentyl)aminobenzamide2회

생성물 1

HCID 159516244-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4,4]nonan-1-yl)-2-fluoro-N-methylbenzamide

시약·촉매·용매 2

HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

A mixture of N-Methyl 2-fluoro-4-(1-cyanocyclopentyl)aminobenzamide (Formula 43) (57 mg, 0.22 mmol) and 4-isothiocyanato-2-trifluoromethyl benzonitrile (0.15 g, 0.65 mmol) in DMF (3 mL) was heated under microwave irradiation (open vessel) at 130° C. for 12 hours. To this mixture was added methanol (20 mL) and aq. 1 N HCl (5 mL). The second mixture was refluxed for 1.5 h. After being cooled to room temperature, the reaction mixture was poured into cold water (50 mL) and extracted with ethyl acetate (50 mL). The organic layer was dried over MgSO4, concentrated and the residue was purified with silica gel column chromatography (dichloromethane:acetone, 95:5) to give 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4.4]nonan-1-yl)-2-fluoro-N-methylbenzamide, NC55 (Formula 44) (8 mg, 7%) as a pale yellowish solid. 1H NMR δ 8.28 (dd, 1H, J=8.4, 8.4 Hz), 7.98 (d, 1H, J=8.3 Hz), 7.96 (d, 1H, J=1.8 Hz), 7.84 (dd, 1H, J=8.3, 1.8 Hz), 7.27 (dd, 1H, J=8.4, 1.8 Hz), 7.17 (dd, 1H, J=11.7, 1.8 Hz), 6.67-6.77 (m, 1H), 3.07 (d, 3H, J=4.3 Hz), 2.32-2.41 (m, 2H), 2.13-2.21 (m, 2H), 1.85-1.96 (m, 2H), 1.49-1.59 (m, 2H).

후처리

  1. temperatureThe second mixture was refluxed for 1.5 h
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue was purified with silica gel column chromatography (dichloromethane:acetone, 95:5)

출처 및 근거

ORD 기록
ord-fbe13d466eaa4b47895af5a34a579515
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08648105B2

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