HCID 178480294, compound → HCID 178480293, compound

HRID 452991Notes

Reaction equation

HRID 452991 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:32])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([N+:29]([O-])=O)[CH:20]=2)/[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:29][C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=1)[C:18](/[N:17]=[C:7]1/[N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[N:9]([CH3:10])[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6]/1)=[O:32]

Participants

4

Reactant 1

HCID 178480294HCID 178480294, compound

Product 1

HCID 178480293HCID 178480293, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of Example 106 (740 mg, 1.63 mmol) and palladium hydroxide (50 mg) in ethyl alcohol (10 mL) was stirred under an atmosphere of hydrogen (balloon) at room temperature for 4 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified on Analogix® Intelliflash280™ (SiO2, 15-100% gradient of solvent A in hexanes, solvent A=10:1:0.5 ethyl acetate:methanol:triethylamine) to provide the title compound (540 mg, 78%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.38 (s, 9H) 1.73-1.83 (m, 3H) 1.89-1.97 (m, 1H) 3.60-3.68 (m, 1H) 3.73-3.81 (m, 1H) 3.89 (s, 3H) 4.18-4.25 (m, 1H) 4.35-4.48 (m, 2H) 5.50 (s, 2H) 6.83-6.86 (m, 2H) 7.56 (d, J=1.70 Hz, 2H); MS (DCI/NH3) m/z 425 (M+H)+. Anal. calcd C21H27F3N4O2.0.5H2O: C, 58.19; H, 6.51; N, 12.33. Found: C, 57.88; H, 6.56; N, 12.63.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified on Analogix® Intelliflash280™ (SiO2, 15-100% gradient of solvent A in hexanes, solvent A=10:1:0.5 ethyl acetate:methanol:triethylamine)

Sources & evidence

ORD record
ord-bd7c38cc7b194772b82257a21b9aa879
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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