HCID 86586785, compound → HCID 86586786, compound

HRID 2088234Notes

Reaction equation

HRID 2088234 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([C:16]3[NH:20][N:19]([CH3:21])[NH:18][N:17]=3)[CH2:15][C@@:9]1([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C@H:10]([O:22][C@H:23]([C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=1)[CH2:24][O:25][CH3:26])[CH2:11][CH2:12]2)C1C=CC=CC=1>[Pd].C(O)(=O)C>[F:35][C:33]([F:34])([F:36])[C:31]1[CH:32]=[C:27]([C@@H:23]([O:22][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:15][C@H:14]3[C:16]2[NH:20][N:19]([CH3:21])[NH:18][N:17]=2)[CH2:24][O:25][CH3:26])[CH:28]=[C:29]([C:37]([F:38])([F:40])[F:39])[CH:30]=1

Participants

4

Reactant 1

HCID 86586785HCID 86586785, compound

Product 1

HCID 86586786HCID 86586786, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1R*)-1-[3,5-bis(trifluoromethyl)phenyl]-2-methoxyethoxy}-6-(2-methyl-1H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 200; 0.03 g, 0.05 mmol), palladium, 5% on carbon (20 mg) and acetic acid (0.5 ml) were placed on the Parr™ apparatus for 2 hours. The mixture was filtered using a Whatman™ 0.2·m filter and concentrated in vacuo. The residue was taken into dichloromethane and washed with NaHCO3 and the phases separated using a bond elute cartridge. The organics were concentrated in vacuo and the title compound isolated as the hydrochloride salt.

Workup

  1. filtrationThe mixture was filtered
  2. filtration0.2·m filter
  3. concentrationconcentrated in vacuo
  4. washwashed with NaHCO3
  5. customthe phases separated
  6. washelute cartridge
  7. concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record
ord-6cc2fe90bc8047438deae6ae6ecfae07
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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