Triethylamine → HCID 49818815, compound

HRID 2407454Notes

Reaction equation

HRID 2407454 reaction equation
[NH2:1][CH:2]([C:7]1[CH:8]=[C:9]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([CH3:21])[CH:14]=2)[CH:10]=[N:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4].C(N(CC)CC)C.[CH2:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30]>C(Cl)Cl>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([C:9]2[CH:8]=[C:7]([CH:2]([NH:1][S:31]([CH2:29][CH3:30])(=[O:33])=[O:32])[C:3]([F:4])([F:6])[F:5])[CH:12]=[N:11][CH:10]=2)=[CH:14][C:15]=1[CH3:21])#[N:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 66788877HCID 66788877, compound

Product 1

HCID 49818815HCID 49818815, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-(1-amino-2,2,2-trifluoroethyl)pyridin-3-yl)-2-methylbenzonitrile (322 mg, 1.105 mmol) in CH2Cl2 (5.5 mL) at 0° C. was added triethylamine (462 μl, 3.32 mmol) and ethanesulfonyl chloride (115 μl, 1.216 mmol). The mixture was stirred for 16 h at room temperature. The mixture was quenched with saturated NaHCO3 and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (10-50% EtOAc/heptane; SNAP25 column) giving the title compound (67 mg, 16%). LC-MS (M+1) 384.1. 1H NMR (400 MHz, MeOD) δ ppm 1.28 (t, J=7.33 Hz, 3H) 2.63 (s, 3H) 2.96-3.19 (m, 2H) 5.47 (q, J=7.89 Hz, 1H) 7.66-7.72 (m, 1H) 7.76-7.79 (m, 1H) 7.81 (d, J=8.02 Hz, 1H) 8.24-8.43 (m, 1H) 8.76 (d, J=2.27 Hz, 1H) 8.93 (d, J=2.21 Hz, 1H).

Workup

  1. customThe mixture was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via Biotage (10-50% EtOAc/heptane; SNAP25 column)

Sources & evidence

ORD record
ord-3f4b3c18078f49a889f5553fc5ed94b9
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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