1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 131735700, compound

HRID 2199632Notes

Reaction equation

HRID 2199632 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[C:11]([NH2:32])=[N:12][CH:13]=[C:14]([C:16]3[N:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[N:20]=3)[CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][C:35]=1[C:43]([F:46])([F:45])[F:44]>O1CCCC1.C(OCC)(=O)C>[NH2:32][C:11]1[C:10]([C:9]#[C:8][C:4]2[CH:3]=[C:2]([NH:1][C:41]([NH:40][C:37]3[CH:38]=[CH:39][C:34]([Cl:33])=[C:35]([C:43]([F:45])([F:44])[F:46])[CH:36]=3)=[O:42])[CH:7]=[CH:6][CH:5]=2)=[CH:15][C:14]([C:16]2[N:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:29])([CH3:31])[CH3:30])([CH3:26])[CH3:27])[N:20]=2)=[CH:13][N:12]=1

Participants

5

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 131735701HCID 131735701, compound

Product 1

HCID 131735700HCID 131735700, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-((3-aminophenyl)ethynyl)-5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)pyridin-2-amine (135 mg, 0.3 mmol, 1 eq) and 4-chloro-3-(trifluoromethyl)phenyl isocyanate (67 mg, 1 eq) in anhydrous tetrahydrofuran (3 mL) was stirred at room temperature and under nitrogen atmosphere for 3 hours. The mixture was then diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine, and dried with anhydrous sodium sulfate. The clear solution was decanted, concentrated under reduced pressure, and the resulting clear oil was dried in vacuo for 5 minutes. It was then treated with a small amount of EtoAc-Hex (1:9), followed by stirring at room temperature for 30 minutes. The white solid that appeared during the process was filtered giving 1-(3-((2-amino-5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)pyridin-3-yl)ethynyl)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea in the amount of 201 mg.

Workup

  1. washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe clear solution was decanted
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting clear oil was dried in vacuo for 5 minutes
  6. additionIt was then treated with a small amount of EtoAc-Hex (1:9)
  7. stirringby stirring at room temperature for 30 minutes
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-eab7f0a997b44f1cbe3a02c42131d01c
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

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