Triethylamine → HCID 86666951, compound

HRID 511030Notes

Reaction equation

HRID 511030 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[C:6]([O:26][CH3:27])=[C:7]([CH:13]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:14])[CH:8]=[C:9]([Cl:12])[C:10]=2[Cl:11])[CH2:2]1.C(N(CC)CC)C.FC(F)(F)S(O[CH2:41][C:42]([F:45])([F:44])[F:43])(=O)=O>C1COCC1.CCOC(C)=O>[CH2:18]([O:17][C:16](=[O:25])[NH:15][CH:13]([C:7]1[CH:8]=[C:9]([Cl:12])[C:10]([Cl:11])=[C:5]([CH:3]2[CH2:4][N:1]([CH2:41][C:42]([F:45])([F:44])[F:43])[CH2:2]2)[C:6]=1[O:26][CH3:27])[CH3:14])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 123840104HCID 123840104, compound

Product 1

HCID 86666951HCID 86666951, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of benzyl [1-(3-azetidin-3-yl-4,5-dichloro-2-methoxyphenyl)ethyl]carbamate (170 mg, 0.43 mmol) in THF (5.8 mL) was treated with triethylamine (110 μL, 0.82 mmol), cooled to 0° C., treated with 2,2,2-trifluoroethyl trifluoromethanesulfonate (150 mg, 0.64 mmol) and stirred at room temperature for 30 minutes. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate, water, and brine, dried with sodium sulfate, filtered and concentrated to give the desired product (190 mg, 92%) that was used without further purification. LCMS for C22H24Cl2F3N2O3 (M+H)+: m/z=491.1, 493.1. Found: 491.1, 493.1.

Workup

  1. washwashed with saturated sodium bicarbonate, water, and brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-470e0e85b8cb449ca6518f7a2b87ec70
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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