HCID 86673872, compound → HCID 68284070, compound

HRID 1527556Notes

Reaction equation

HRID 1527556 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C:9](=[O:23])[CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:20]([NH2:22])=[O:21])[CH:12]=2)[C@H:6]([C:24](=[O:35])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[F:34])[CH2:5]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:8][N:7]([C:9](=[O:23])[CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:20]([NH2:22])=[O:21])[CH:12]=2)[C@H:6]([C:24](=[O:35])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[F:34])[CH2:5]1

Participants

4

Reactant 1

HCID 86673872HCID 86673872, compound

Product 1

HCID 68284070HCID 68284070, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-{2-[(2S,4S)-4-azido-2-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-indole-1-carboxylic acid amide (80 mg, 0.161 mmol) in MeOH (8 mL) was hydrogenated over Pd/C 10% (8 mg, 10% w/w) at RT (1 atm). The reaction mixture was filtered through a 0.45 microns filter and concentrated under reduced pressure to give the title compound as colorless foam. MS (LC/MS): 472 [M+H]+; tR (HPLC conditions b) 2.94 min.

Workup

  1. filtrationThe reaction mixture was filtered through a 0.45 microns
  2. filtrationfilter
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e5c09cfec834a52a705800affff90a6
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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