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Trimethylsilyl iodide → N1-[5-(2-Fluoro-4-trifluoromethylphenyl)oxazol-2-yl]-5,6,7,8-tetrahydronaphthalene-1,7-diamine

HRID 600813
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600813
I[Si](C)(C)C.C(OC(=O)[NH:12][CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[C:16]([NH:23][C:24]3[O:25][C:26]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:30]=4[F:39])=[CH:27][N:28]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14]1)(C)(C)C>C(Cl)Cl>[F:39][C:30]1[CH:31]=[C:32]([C:35]([F:36])([F:37])[F:38])[CH:33]=[CH:34][C:29]=1[C:26]1[O:25][C:24]([NH:23][C:16]2[C:15]3[CH2:14][CH:13]([NH2:12])[CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)=[N:28][CH:27]=1
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Komponenten

4

Edukt 2

HCID 85247Trimethylsilyl iodideHCID 67228763{8-[5-(2-Fluoro-4-trifluoromethylphenyl)oxazol-2-ylamino]-1,2,3,4-tetrahydronaphthalen-2-yl}carbamic acid tert-butyl ester

Produkt 1

HCID 11964242N1-[5-(2-Fluoro-4-trifluoromethylphenyl)oxazol-2-yl]-5,6,7,8-tetrahydronaphthalene-1,7-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Iodotrimethylsilane (52 mg, 0.260 mmol) was added dropwise to a solution of the product of Example 22B (107 mg, 0.218 mmol) in 1 mL CH2Cl2 at ambient temperature. After 15 minutes the reaction was diluted with CH2Cl2 and quenched with 1N aq NaOH solution. The mixture was stirred 15 minutes and then poured into water. The separated organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was triturated with Et2O/hexanes and the solid collected by vacuum filtration and dried under high vacuum. The result was 36 mg (42%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 9.42 (br s, 1H), 7.75 (m, 3H), 7.52 (d, J=8.1 Hz, 1H), 7.44 (d, J=3.7 Hz, 1H), 7.11 (t, J=7.5 Hz, 1H), 6.88 (d, J=7.5 Hz, 1H), 3.05-2.70 (m, 4H), 2.30 (m, 1H), 1.86 (m, 1H), 1.70 (br s, 2H), 1.43 (m, 1H); MS (ESI+) m/z 392 (M+H)+.

Aufarbeitung

  1. customquenched with 1N aq NaOH solution
  2. additionpoured into water
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was triturated with Et2O/hexanes
  8. filtrationthe solid collected by vacuum filtration
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-917d77ee193346e4a5235a8a588d3b5b
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902236B2

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