Ethyl chloroformate → HCID 86730305, compound

HRID 1622567Notes

Reaction equation

HRID 1622567 reaction equation
Cl.[F:2][C:3]([F:23])([F:22])[C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[NH2:11])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[C:33](Cl)(=[O:37])[O:34][CH2:35][CH3:36]>CC#N.C([O-])(O)=O.[Na+]>[CH2:35]([O:34][C:33](=[O:37])[NH:11][C@@H:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([F:22])([F:2])[F:23])=[CH:9][CH:8]=1)[C:12]1[C:17]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:36]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 86687962(S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine Hydrochloride2×

Product 1

HCID 86730305HCID 86730305, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of (S)-(4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)-pyridin-2-yl)methanamine (Intermediate 1) (0.0610 g, 0.190 mmol) and DIPEA (0.066 mL, 0.381 mmol) in MeCN (1 mL) was added ethyl carbonochloridate (0.027 mL, 0.286 mmol). The mixture was then stirred at rt overnight. The mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated in vacuo. The resulting product was purified by silica gel chromatography: 5-50% EtOAc-hexanes to give the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 8.83 (d, J=4.30 Hz, 1H), 7.99 (d, J=7.24 Hz, 1H), 7.46-7.60 (m, 4H), 7.40 (dd, J=7.73, 4.79 Hz, 1H), 6.54 (d, J=7.43 Hz, 1H), 6.41 (d, J=8.22 Hz, 1H), 4.11 (q, J=7.17 Hz, 2H), 1.17-1.30 (m, 3H). MS (ESI pos. ion) m/z: 393.0 (M+H).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-da32005e819d47da9310e7338973fca9
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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