Triethylamine → HCID 86680473, compound

HRID 240465Notes

Reaction equation

HRID 240465 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C@H:10]2[CH2:25][N:13]3[CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][C@@H:12]3[CH2:11]2)=[N:7][CH:8]=1.C(N(CC)CC)C.[F:35][C:36]([F:48])([F:47])[C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1>ClCCl.FC(F)(F)C(O)=O>[F:48][C:36]([F:35])([F:47])[C:37]1[CH:38]=[CH:39][C:40]([S:43]([N:16]2[CH2:15][CH2:14][N:13]3[CH2:25][C@H:10]([O:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:27])[F:26])=[CH:8][N:7]=4)[CH2:11][C@H:12]3[CH2:17]2)(=[O:45])=[O:44])=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 86680474HCID 86680474, compound

Product 1

HCID 86680473HCID 86680473, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from Example 226A (0.14 g, 0.361 mmol) in dichloromethane (2.5 mL) and trifluoroacetic acid (2.5 mL) was stirred at room temperature for 2 hours and then concentrated in vacuo. The residue was dissolved in a mixture of dichloromethane (3 mL) and triethylamine (0.30 mL, 2.17 mmol), and 4-(trifluoromethyl)benzene-1-sulfonyl chloride (0.097 g, 0.398 mmol) was added. The resulting mixture was stirred at room temperature for 16 hours, and then it was partitioned between water and dichloromethane. The organic extract was dried over Na2SO4. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-3% ethyl acetate in heptane to give the title compound as a colorless solid (0.132 g, 74%). 1H NMR (300 MHz, CDCl3) δ ppm 1.72-1.90 (m, 1H) 1.91-2.06 (m, 1H) 2.06-2.20 (m, 1H) 2.33 (dd, J=9.49, 4.75 Hz, 1H) 2.37-2.70 (m, 3H) 3.00 (d, J=7.80 Hz, 1H) 3.58-3.73 (m, 1H) 3.77 (d, J=8.82 Hz, 1H) 3.92 (d, J=10.17 Hz, 1H) 5.41 (q, J=6.22 Hz, 1H) 6.79 (d, J=8.82 Hz, 1H) 7.76 (dd, J=8.65, 2.54 Hz, 1H) 7.79-7.94 (m, 4H) 8.39 (d, J=2.37 Hz, 1H); MS (ESI) m/z 496 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionwas added
  3. customit was partitioned between water and dichloromethane
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-3% ethyl acetate in heptane

Sources & evidence

ORD record
ord-cf63c3db9c254c5d8da7bff4f457c29e
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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