HCID 86644572, compound → HCID 86644571, compound

HRID 1891216Notes

Reaction equation

HRID 1891216 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:18]2[N:23]=[C:22]([C:24]3[CH:50]=[CH:49][CH:48]=[CH:47][C:25]=3[O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH2:35][CH2:36][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38][CH:39]=4)=[CH:30][CH:29]=3)[CH:21]=[CH:20][CH:19]=2)[C:10]=1[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[H][H]>CCOC(C)=O.[Pt](=O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:18]2[N:23]=[C:22]([C:24]3[CH:50]=[CH:49][CH:48]=[CH:47][C:25]=3[O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]4[CH2:35][CH2:36][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:44])[CH3:45])=[O:41])[CH2:38][CH2:39]4)=[CH:30][CH:29]=3)[CH:21]=[CH:20][CH:19]=2)[C:10]=1[C:11]([F:16])([F:17])[C:12]([F:13])([F:14])[F:15])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 86644572HCID 86644572, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86644571HCID 86644571, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of the title compound from Example 8 Step E (549 mg, 0.79 mmol) in EtOAc (15 mL) was added platinum(IV) oxide (200 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 20 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. The filtrate was then concentrated in vacuo. Purification by chromatography on silica gel (0 to 40% EtOAc in hexanes, then 40 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 700.8 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.21 (s, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.86-7.82 (m, 2H), 7.38-7.35 (m, 2H), 7.30 (d, J=8.0 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 7.09-7.06 (m, 2H), 5.12 (s, 2H), 4.37 (q, J=7.0 Hz, 2H), 4.29-4.20 (br m, 2H), 2.83-2.76 (br m, 2H), 2.68-2.63 (m, 1H), 1.84-1.81 (m, 2H), 1.49 (s, 9H), 1.38 (t, J=7.0 Hz, 3H).

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. concentrationThe filtrate was then concentrated in vacuo
  7. customPurification by chromatography on silica gel (0 to 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-bc862912cc2140c6a2cbf31d28428f85
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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