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Hydrochloric Acid → 4-(4-(7-(4-Cyano-3-(trifluoromethyl)phenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-an-5-yl)-2-fluorophenyl)-n-methylbutanamide

HRID 1192870
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HRID 1192870 반응식
[C:1]([C:3]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[C:10]([F:21])[CH:9]=2)[CH2:6][CH2:5][CH2:4]1)#N.[N:22]([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=1)=[C:23]=[S:24].C[OH:38].Cl>CN(C=O)C.O>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:22]2[C:1](=[O:38])[C:3]3([CH2:6][CH2:5][CH2:4]3)[N:7]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[C:10]([F:21])[CH:9]=3)[C:23]2=[S:24])=[CH:26][C:27]=1[C:33]([F:34])([F:36])[F:35])#[N:30]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 689425014-(4-(1-Cyanocyclobutylamino)-2-fluorophenyl)-N-methylbutanamide

생성물 1

HCID 252684834-(4-(7-(4-Cyano-3-(trifluoromethyl)phenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-an-5-yl)-2-fluorophenyl)-n-methylbutanamide수율 62%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of 4-(4-(1-Cyanocyclobutylamino)-2-fluorophenyl)-N-methylbutanamide (79) (7 mg, 0.02 mmol) and 4-isothiocyanato-2-trifluoromethylbenzonitrile (96) (12 mg, 0.05 mmol) in DMF (1 mL) was heated to 80° C. using microwave for 16 h. To this mixture was added methanol (3 mL) and aq. 1 N HCl (3 mL). The second mixture was refluxed for 1.5 h. After being cooled to room temperature, the reaction mixture was poured into cold water (30 mL) and extracted with ethyl acetate (30 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-(4-(7-(4-Cyano-3-(trifluoromethyl)phenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-an-5-yl)-2-fluorophenyl)-N-methylbutanamide (78) [ND-7] (8 mg, 62%) as a pale yellowish solid: 1H NMR δ 7.98 (d, 1H, J=8.2 Hz) 7.97 (d, 1H, J=2.0 Hz) 7.84 (dd, 1H, J=8.2, 2.0 Hz), 7.43 (dd, 1H, J=8.0, 8.0 Hz), 7.06 (dd, 1H, J=8.0, 2.0 Hz), 7.02 (dd, 1H, J=9.7, 2.0 Hz), 2.83 (d, 3H, J=4.8 Hz) 2.78 (t, 2H, J=7.7 Hz) 2.63-2.71 (m, 2H), 2.51-2.62 (m, 2H), 2.27 (t, 2H, J=7.3 Hz) 2.18-2.27 (m, 1H), 2.00-2.09 (m, 2H), 1.66-1.76 (m, 1H); 13C NMR δ 179.9, 174.7, 172.8, 161.2 (d, J=247 Hz), 137.0, 135.2, 134.1 (d, J=9.6 Hz), 133.6 (q, J=33.7 Hz), 132.1, 131.9 (d, J=5.6 Hz), 130.8 (d, J=15.2 Hz), 127.1, 125.7 (d, J=3.9 Hz), 121.9 (q, J=272 Hz), 117.3 (d, J=22.3 Hz), 114.8, 110.0, 67.4, 35.8, 31.5, 28.3, 26.4, 25.6, 13.7.

후처리

  1. customfor 16 h
  2. temperatureThe second mixture was refluxed for 1.5 h
  3. temperatureAfter being cooled to room temperature
  4. extractionextracted with ethyl acetate (30 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customthe residue was purified with silica gel column chromatography (dichloromethane:acetone, 95:5)

출처 및 근거

ORD 기록
ord-827d5f0e44d148a3b42985acffb65ef6
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680291B2

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