Trifluoroacetic acid → HCID 86670641, compound

HRID 1625027Notes

Reaction equation

HRID 1625027 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:10]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]3[CH2:42][O:41][CH2:40]3)=[CH:34][CH:33]=2)=[CH:11][C:12](=[O:31])[N:13]([CH2:15][CH2:16][C@@:17]([S:27]([CH3:30])(=[O:29])=[O:28])([NH:19][O:20]C2CCCCO2)[CH3:18])[CH:14]=1>C(Cl)Cl>[F:8][C:9]1[C:10]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]3[CH2:40][O:41][CH2:42]3)=[CH:34][CH:33]=2)=[CH:11][C:12](=[O:31])[N:13]([CH2:15][CH2:16][C@:17]([NH:19][OH:20])([S:27]([CH3:30])(=[O:29])=[O:28])[CH3:18])[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86670642HCID 86670642, compound

Product 1

HCID 86670641HCID 86670641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of 5-fluoro-1-{(3R)-3-(methylsulfonyl)-3-[(tetrahydro-2H-pyran-2-yloxy)amino]butyl}-4-[4-(oxetan-3-yloxy)phenyl]pyridin-2(1H)-one (164 mg, 0.304 mmol) in DCM (10 mL). The reaction was allowed to stir at rt overnight and then concentrated under vacuum. The residue was re-dissolved in dichloromethane and n-heptane and concentrated again to afford the title compound as a solid. (113 mg, 82%). MS (LCMS) m/z 455.1 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.69 (s, 3 H) 2.35 (ddd, J=13.66, 10.63, 5.17 Hz, 1 H) 2.53-2.67 (m, 1 H) 3.09 (s, 3 H) 3.91 (ddd, J=12.98, 10.63, 5.27 Hz, 1 H) 4.16-4.30 (m, 1 H) 4.69 (dd, J=7.51, 4.78 Hz, 2 H) 5.02 (t, J=6.73 Hz, 2 H) 5.33 (t, J=5.46 Hz, 1 H) 6.58 (d, J=7.42 Hz, 1 H) 6.85-6.91 (m, 2 H) 7.55 (dd, J=8.68, 1.85 Hz, 2 H) 7.80 (d, J=6.24 Hz, 1 H).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was re-dissolved in dichloromethane
  3. concentrationn-heptane and concentrated again

Sources & evidence

ORD record
ord-71bf516a6a13413b884e91d73c4510d2
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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