(Diethylamino)sulfur trifluoride → HCID 118235835, compound

HRID 627004Notes

Reaction equation

HRID 627004 reaction equation
CCN(S(F)(F)[F:7])CC.[F:10][CH:11]([F:41])[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]1[N:24]2[CH:25]=[C:26]([C:30]3[CH:31]=[N:32][C:33]([C:36](O)([CH3:38])[CH3:37])=[N:34][CH:35]=3)[C:27]([F:29])=[CH:28][C:23]2=[N:22][C:21]=1[CH3:40]>O1CCCC1>[F:41][CH:11]([F:10])[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]1[N:24]2[CH:25]=[C:26]([C:30]3[CH:31]=[N:32][C:33]([C:36]([F:7])([CH3:37])[CH3:38])=[N:34][CH:35]=3)[C:27]([F:29])=[CH:28][C:23]2=[N:22][C:21]=1[CH3:40]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 118235452HCID 118235452, compound

Product 1

HCID 118235835HCID 118235835, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DAST (0.04 mL, 0.34 mmol) was added to a solution of Example 173 (0.1 g, 0.23 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature under N2 gas. The mixture was stirred at room temperature for 2 h, quenched with water (5 mL) and poured onto saturated aqueous NaHCO3 solution (10 mL). The crude residue was extracted with EtOAc (3×10 mL), dried (MgSO4) and concentrated in vacuo. The resulting light yellow glass was purified by chromatography on silica (Biotage, 10 g cartridge), eluting with 0 to 100% EtOAc in heptanes. The resulting crude off white gum was further purified by preparative HPLC (preparative method C, neutral) to give the title compound (0.031 g, 31%) as a pale orange glass. δH (500 MHz, CDCl3) 8.80 (d, J 1.4 Hz, 2H), 7.79 (d, J 7.0 Hz, 1H), 7.37 (d, J 10.6 Hz, 1H), 7.30-7.27 (m, 1H), 7.17 (d, J 7.9 Hz, 1H), 7.11 (t, J 7.5 Hz, 1H), 6.90 (dd, J 7.7, 1.2 Hz, 1H), 6.62 (t, J 73.6 Hz, 1H), 4.29 (s, 2H), 2.52 (s, 3H), 1.83 (d, J 21.7 Hz, 6H). Method D HPLC-MS: MH+ m/z 445, RT 2.24 minutes.

Workup

  1. customquenched with water (5 mL)
  2. additionpoured onto saturated aqueous NaHCO3 solution (10 mL)
  3. extractionThe crude residue was extracted with EtOAc (3×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting light yellow glass was purified by chromatography on silica (Biotage, 10 g cartridge)
  7. washeluting with 0 to 100% EtOAc in heptanes
  8. customThe resulting crude off white gum was further purified by preparative HPLC (preparative method C, neutral)

Sources & evidence

ORD record
ord-a40fcd048bfe479fb8887e6c924724a7
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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