HCID 86644567, compound → HCID 86644566, compound

HRID 1891213Notes

Reaction equation

HRID 1891213 reaction equation
[F:1][CH:2]([F:50])[C:3]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([N:36]3[C:40]([C:41]([F:44])([F:43])[F:42])=[C:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:38]=[N:37]3)[N:31]=2)[C:4]=1[O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=2)=[CH:9][CH:8]=1.[H][H]>CCOC(C)=O.[Pt]=O>[F:50][CH:2]([F:1])[C:3]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([N:36]3[C:40]([C:41]([F:44])([F:43])[F:42])=[C:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:38]=[N:37]3)[N:31]=2)[C:4]=1[O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:17][CH2:18]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 86644567HCID 86644567, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86644566HCID 86644566, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of the title compound from Example 7 Step E (115 mg, 0.17 mmol) in EtOAc (5 mL) was added platinum oxide (22 mg). The reaction flask was fitted with a hydrogen balloon attached to a 3-way adapter. The reaction mixture was then evacuated and back-filled with hydrogen. After this process was repeated three times, the reaction mixture was placed under a hydrogen atmosphere, and was stirred vigorously. After 45 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (0 to 30% EtOAc in hexanes, 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 701.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.15 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 8.01-7.92 (m, 2H), 7.68 (dd, J=8.0, 6.0 Hz, 2H), 7.39 (t, J=8.0 Hz, 1H), 7.15 (dd, J=12.5, 8.5 Hz, 4H), 6.94 (t, 2JH-F=55.5 Hz, 1H), 4.57 (s, 2H), 4.40 (q, J=7.0 Hz, 2H), 4.34-4.16 (br m, 2H), 2.90-2.72 (br m, 2H), 2.68-2.60 (m, 1H), 1.86-1.74 (m, 2H), 1.66-1.56 (m, 2H), 1.49 (s, 9H), 1.40 (t, J=7.0 Hz, 1H).

Workup

  1. customattached to a 3-way adapter
  2. customThe reaction mixture was then evacuated
  3. additionback-filled with hydrogen
  4. filtrationthe reaction mixture was filtered though Celite
  5. washrinsing with EtOAc
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography on silica gel (0 to 30% EtOAc in hexanes, 30 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c3d7e4994fc3483bb98c07c0bb43bad4
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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