Ethanamine, 2,2,2-trifluoro- → HCID 86613590, compound

HRID 1365527Notes

Reaction equation

HRID 1365527 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]([NH:28][C:29](=O)[O:30]C(C)=C)([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:35][C:36]([F:40])([F:39])[CH2:37][NH2:38]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@:12]([NH:28][C:29]([NH:38][CH2:37][C:36]([F:40])([F:39])[F:35])=[O:30])([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=2)[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 58920290HCID 58920290, compound

Product 1

HCID 86613590HCID 86613590, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of prop-1-en-2-yl 1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(5-methoxypyridin-2-yl)-2-phenylethylcarbamate (100 mg, 0.210 mmol) in THF (200 μl) was added 2,2,2-trifluoroethanamine (200 μl, 2.1 mmol). The resulting mixture was stirred at 100° C. under microwave irradiation for 1200 sec then at 150° C. for 1800 sec. The solvent was evaporated under reduced pressure and the residue was purified by ISCO chromatography (40 g column) using hexanes/EtOAc (0-100% over 12 min) to give (R)-1-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(5-methoxypyridin-2-yl)-2 phenylethyl)-3-(2,2,2-trifluoroethyl)urea as white powder (68 mg, 63% yield) LCMS: RT=2.03 min [M+H] 516.2 (LCMS Method 1); HPLC: RT=3.24 min, Purity 98% (HPLC Method 2); NMR: 400 MHz 1H (CD3OD) 8.30 ppm, 1H, s; 7.98 ppm, 1H, dd, J=4.55, 1.26 Hz; 7.46ppm, 1H, s; 7.39 ppm, 2H, m; 7.30 ppm, 1H, m; 7.21 ppm, 1H, m; 7.00 ppm, 3H, m; 6.66 ppm, 2H, m; 4.18 ppm, 2H, m; 3.90 ppm, 1H, m; 3.63 ppm, 4H, m.

Workup

  1. waitat 150° C. for 1800 sec
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by ISCO chromatography (40 g column)
  4. customhexanes/EtOAc (0-100% over 12 min)

Sources & evidence

ORD record
ord-1b6239030fb94199a88dd7c64317ed91
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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