HCID 86628107, compound → HCID 86628109, compound

HRID 2245243Notes

Reaction equation

HRID 2245243 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C@@H:13]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH3:14])[C@@H:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@@H:7]1[CH2:36][NH:37]CC1C=CC=CC=1)(=[O:3])[CH3:2]>C(O)C.[OH-].[OH-].[Pd+2]>[C:1]([O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C@@H:13]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:16]=2)[CH3:14])[C@@H:8]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[C@@H:7]1[CH2:36][NH2:37])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86628107HCID 86628107, compound

Product 1

HCID 86628109HCID 86628109, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of the crude oil from Step M in 50 mL ethanol was added 0.2 g (20% by weight) of 10% Pd(OH)2—C. The mixture was hydrogenated at 50 PSi for 16 hr at room temperature. The catalyst was filtered through a filter aid pad. The solvent of the filtrate was removed under vacuum to give the title compound (0.35 g). 1H-NMR (CDCl3) δ: 7.70 (1H, s), 7.23 (2H, m), 7.21 (2H, s), 6.98 (2H, m), 4.48 (1H, q, J=6.5 Hz), 4.15 (2H, m), 3.27 (1H, m), 2.86 (2H, m), 2.53 (1H, d, J=11.0 Hz), 2.36 (1H, m), 2.07 (3H, s), 1.98 (2H, m), 1.75 (1H, m), 1.55-1.27 (2H, m), 1.37 (3H, d, J=6.4 Hz). MS: (MH)+ 536.5.

Workup

  1. filtrationThe catalyst was filtered through a filter aid pad
  2. customThe solvent of the filtrate was removed under vacuum

Sources & evidence

ORD record
ord-f49321c9e6d34a319e1b933f7897bb3d
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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