HCID 67248450, compound → HCID 67250238, compound

HRID 1035314Notes

Reaction equation

HRID 1035314 reaction equation
[CH:1]([C:3]1[C:13]2[O:12][CH2:11][CH2:10][C@H:9]3[CH2:14][NH:15][CH2:16][CH2:17][N:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH2:2]>O1CCCC1.[Pd]>[CH2:1]([C:3]1[C:13]2[O:12][CH2:11][CH2:10][C@H:9]3[CH2:14][NH:15][CH2:16][CH2:17][N:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67248450HCID 67248450, compound

Product 1

HCID 67250238HCID 67250238, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 237A (60.8 mg, 0.264 mmol) in tetrahydrofuran (20 mL) was added to 5% Pd—C (wet, 18.24 mg, 0.171 mmol). The solution was stirred under H2 (30 psi) for 16 hours at ambient temperature. The solution was then filtered through a nylon membrane and concentrated. Purification via HPLC (ammonium acetate method) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 6.72-6.92 (m, 3H), 4.27-4.42 (m, 1H), 4.04-4.16 (m, 1H), 2.69-3.15 (m, 7H), 2.43-2.59 (m, 2H), 1.76-2.03 (m, 2H), 1.08 (t, J=7.54 Hz, 3H); MS (ESI+) m/z 233 (M+H)+.

Workup

  1. filtrationThe solution was then filtered through a nylon membrane
  2. concentrationconcentrated
  3. customPurification via HPLC (ammonium acetate method)

Sources & evidence

ORD record
ord-06d9281588de4a14bebb913c20fb2cd8
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

Loading…