HCID 178456106, compound → HCID 178456107, compound

HRID 1931111Notes

Reaction equation

HRID 1931111 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)/[C:7](=[N:17]/[C:18](=[O:35])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=2[O:29][CH2:30][C@@H:31]([OH:34])[CH:32]=[CH2:33])/[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)/[C:7](=[N:17]/[C:18](=[O:35])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=2[O:29][CH2:30][C@@H:31]([OH:34])[CH2:32][CH3:33])/[CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 1

HCID 178456106HCID 178456106, compound

Product 1

HCID 178456107HCID 178456107, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of Example 107 (40 mg, 0.081 mmol) and 10% Pd/C (20 mg) was stirred under an atmosphere of hydrogen (balloon) at room temperature for 2 hours. The mixture was filtered through Celite, and the filtrate was concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 50% hexanes/EtOAc to 100% EtOAc to 9:1:0.1 EtOAc:MeOH:Et3N) to afford 27 mg (67%) of the title compound. 1H NMR (500 MHz, chloroform-d) δ ppm 1.00 (t, J=7.32 Hz, 3H) 1.42 (s, 9H) 1.60 (s, 3H) 1.65-1.80 (m, 2H) 1.81-1.91 (m, 1H) 1.97-2.08 (m, 1H) 3.66-3.81 (m, 2H) 3.85-3.92 (m, 3H) 3.87-3.97 (m, 1H) 4.17 (s, 1H) 4.31 (d, J=5.49 Hz, 1H) 4.39 (d, J=7.93 Hz, 1H) 4.55 (d, J=14.34 Hz, 1H) 6.62 (s, 1H) 6.95-7.16 (m, 2H) 7.51 (s, 1H) 8.09 (s, 1H); MS (DCI/NH3) m/z 498 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ec2b10b902f54d83a63a06f2f44e019a
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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