Trifluoroacetic acid → HCID 86604869, compound

HRID 1432006Notes

Reaction equation

HRID 1432006 reaction equation
[C:1]1([S:7]([N:10]2[CH:15]=[CH:14][NH:13][C:12](=[O:16])[C@H:11]2[CH2:17][C:18]#[CH:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][NH:13][C:12](=[O:16])[C@H:11]2[CH2:17][C:18]#[CH:19])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86604865HCID 86604865, compound

Product 1

HCID 86604869HCID 86604869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (R)-4-(benzenesulfonyl)-3-(Prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one (2.7 g, 9.77 mmol) and Et3SiH (16 mL, 97.7 mmol) in CH2Cl2 (30 mL) was added TFA (16.7 g, 147 mmol). The reaction mixture was refluxed for 24 h and cooled. The mixture was concentrated and triturated with ether. The solid was filtered and air-dried to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 2.02 (s, 1H), 2.45 (s, 3H), 2.85 (m, 1H), 2.97 (m, 1H), 3.24 (m, 2H), 3.81 (m, 2H), 4.48 (t, 4.7 Hz, 1H), 6.47 (s, 1H), 7.55 (m, 3H), 7.78 (d, 8.3 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. temperaturecooled
  3. concentrationThe mixture was concentrated
  4. customtriturated with ether
  5. filtrationThe solid was filtered
  6. customair-dried

Sources & evidence

ORD record
ord-2b0e00199f2342c4bed53c868b821af4
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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