Trimethylsilyl isocyanate → HCID 11583150, compound

HRID 1173420Notes

Reaction equation

HRID 1173420 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][N:11]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)=[CH:4][CH:3]=1.[Si]([N:33]=[C:34]=[O:35])(C)(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([N:11]([CH2:24][C:25]([F:26])([F:27])[F:28])[CH2:10][CH2:9][O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:34]([NH2:33])=[O:35])=[CH:3][CH:4]=2)=[CH:13][C:14]=1[C:20]([F:21])([F:22])[F:23])#[N:17]

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanate2×HCID 86623733HCID 86623733, compound

Product 1

HCID 11583150HCID 11583150, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[{2-[(4-aminophenyl)oxy]ethyl}(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.105 g, 0.25 mmol; Example 28A) in dry CH2Cl2 (5 mL) at room temp, under N2, was added TMS-isocyanate (0.05 mL, 0.29 mmol) and the mixture was stirred overnight. After 12 h, an additional portion of TMS-isocyanate (0.09 mL, 0.58 mmol) and DMAP (0.003 g, 0.025 mmol) was added and stirring continued. After 2 h, the mixture was quenched with 10% v/v HCl and the whole extracted with EtOAc (×3). Combined organics were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), followed by preparative RP-HPLC (C18 column, MeCN/water), affording 0.0448 g of the title compound as a colorless gum: MS (ES) m/z 447 (M+1).

Workup

  1. waitAfter 12 h
  2. stirringstirring
  3. waitAfter 2 h
  4. customthe mixture was quenched with 10% v/v HCl
  5. extractionthe whole extracted with EtOAc (×3)
  6. washCombined organics were washed (water, brine)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-2ed1eac48ac947d3afbfbe136d0f11f5
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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