Triethylamine → HCID 57753224, compound

HRID 1930853Notes

Reaction equation

HRID 1930853 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12]O)=[C:4]([CH2:14]O)[CH:3]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.C(N(CC)C(C)C)(C)C.[C:37]1([C:43]([NH2:56])([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C1C=CN=CC=1)C.ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9])[CH2:12][N:56]([C:43]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[CH2:14]2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 138598TritylamineHCID 57753319HCID 57753319, compound

Product 1

HCID 57753224HCID 57753224, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1.56 mmol (4-fluoro-2-hydroxymethyl-5-trifluoromethyl-phenyl)-methanol and 0.08 mmol DMAP in 5 ml dichloromethane at 0° C. were added dropwise 3.28 mmol methanesulfonyl chloride and 6.25 mmol triethylamine. The mixture was stirred at 0° C. for 1 h, and then heated quenched with water. The mixture was extracted with dichloromethane and the organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in DMF and then 4.68 mmol N,N-diisopropylethylamine and 2.03 mmol triphenylmethylamine were added sequentially. The mixture was heated at 60° C. for 1 day and then at 80° C. for a further day. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: ethyl acetate/heptane) to afford the title compound as a white amorphous solid (23% yield). EI-MS (m/e): 370.1 ([M-Ph]+, 100%).

Workup

  1. temperatureheated
  2. customquenched with water
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in DMF
  7. temperatureThe mixture was heated at 60° C. for 1 day
  8. waitat 80° C. for a further day
  9. temperatureThe mixture was then cooled to room temperature
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography on silica gel (eluant: ethyl acetate/heptane)

Sources & evidence

ORD record
ord-812b71c6307347a9b7500b866ee1f75e
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

Loading…