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

HRID 1785576Notes

Reaction equation

HRID 1785576 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-cb420747152046439dfc72ae869b1f80
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

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