HCID 58617415, compound → HCID 58617389, compound

HRID 2223152Notes

Reaction equation

HRID 2223152 reaction equation
[CH:1]1([N:5]([CH3:47])[CH:6]([CH3:46])[CH2:7][CH2:8][N:9]([C@@H:24]([C:26]2[N:27]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH3:45])=[CH:39][CH:38]=3)[C:28](=[O:36])[C:29]3[CH:35]=[CH:34][CH:33]=[N:32][C:30]=3[N:31]=2)[CH3:25])[C:10](=[O:23])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([N:5]([CH3:47])[CH:6]([CH3:46])[CH2:7][CH2:8][N:9]([C@@H:24]([C:26]2[N:27]([C:37]3[CH:38]=[CH:39][C:40]([O:43][CH2:44][CH3:45])=[CH:41][CH:42]=3)[C:28](=[O:36])[C:29]3[CH2:35][CH2:34][CH2:33][NH:32][C:30]=3[N:31]=2)[CH3:25])[C:10](=[O:23])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:13]=2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 58617415HCID 58617415, compound

Product 1

HCID 58617389HCID 58617389, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

E5 (33 mg, 0.048 mmol) was dissolved in methanol and degassed with nitrogen for 5 min. Palladium (10% wt. on C, 33 mg) was added, then the reaction was placed under hydrogen atmosphere with a balloon. It was stirred for 2 h at room temperature, then filtered through Celite, and concentrated in vacuo. Purified by reverse-phase HPLC to yield 16 mg, a colorless solid, 4. MS (MH+): 658.3. 1H NMR (400 MHz; CDCl3; T=298 K): δ 7.40 (m, 1H), 7.14 (m, 4H), 6.89 (dd, 2H, J=8.7, 22.9 Hz), 5.21 (m, 1H), 4.81 (m, 1H), 4.02 (dd, 2H, J=15.9, 9.9 Hz), 3.57 (d, 1H, J=9.6 Hz), 3.39 (m, 2H), 3.21 (m, 2H), 3.03 (m, 1H), 2.76 (d, 1H, J=14.8 Hz), 2.56 (m, 2H), 2.20 (dd, 1H, J=25.0, 15.8 Hz), 1.97 (d, 3H, J=11.2 Hz), 1.88 (s, 3H), 1.74 (m, 3H), 1.64 (m, 3H), 1.40 (d, 4H, J=10.8 Hz), 1.30 (d, 6H, J=18.8 Hz) ppm.

Workup

  1. customdegassed with nitrogen for 5 min
  2. additionPalladium (10% wt. on C, 33 mg) was added
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. customPurified by reverse-phase HPLC
  6. customto yield 16 mg

Sources & evidence

ORD record
ord-c230833eb2484d82a3bb9a74d53ad00e
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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