HCID 58660098, compound → HCID 58660103, compound

HRID 29729Notes

Reaction equation

HRID 29729 reaction equation
[C:1]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[C@H:7]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[C:30]([CH3:32])[C:29]([CH3:33])=[CH:28][C:27]=3[C@@H:34]([NH:37]C(=O)OCC3C=CC=CC=3)[CH2:35][CH3:36])[CH2:22][CH2:21]2)=[O:19])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[C@H:7]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[C:30]([CH3:32])[C:29]([CH3:33])=[CH:28][C:27]=3[C@@H:34]([NH2:37])[CH2:35][CH3:36])[CH2:22][CH2:21]2)=[O:19])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58660098HCID 58660098, compound

Product 1

HCID 58660103HCID 58660103, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of amine 112 (910 mg, 1.41 mmol) and 10% Pd on carbon (91 mg of “Degussa type”), in ethanol/glacial acetic acid (1:1, 20 mL) was hydrogenated at atmospheric pressure for approximately 3 h. The resulting mixture was filtered through a short column of Celite®, eluting copiously with ethanol. The filtrate was evaporated and the residue was partitioned between DCM and saturated aqueous sodium bicarbonate. The organic layer was separated and the aqueous phase was re-extracted twice with DCM. The combined organic extracts were washed with water, brine, dried (MgSO4), filtered, and the filtrate concentrated in vacuo to afford 113 as a colorless oil which was used in the next step without further purification.

Workup

  1. filtrationThe resulting mixture was filtered through a short column of Celite®
  2. washeluting copiously with ethanol
  3. customThe filtrate was evaporated
  4. customthe residue was partitioned between DCM and saturated aqueous sodium bicarbonate
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was re-extracted twice with DCM
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2c282042716e4a1a95f5d78da4373836
Source dataset
uspto-grants-2008_09
Patent number
US07419990B2

Reaction notes

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