(1R,3S,5R)-2-[2-(3-Acetyl-5-benzyloxy-indazol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoromethoxy-phenyl)-amide → (1R,3S,5R)-2-[2-(3-Acetyl-5-hydroxy-indazol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoromethoxy-phenyl)-amide

HRID 1527607Notes

Reaction equation

HRID 1527607 reaction equation
[F:1][C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:13][C:14]([C@@H:16]1[CH2:21][C@@H:20]2[C@@H:18]([CH2:19]2)[N:17]1[C:22](=[O:44])[CH2:23][N:24]1[C:32]2[C:27](=[CH:28][C:29]([O:33]CC3C=CC=CC=3)=[CH:30][CH:31]=2)[C:26]([C:41](=[O:43])[CH3:42])=[N:25]1)=[O:15]>CO.[Pd]>[F:1][C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:13][C:14]([C@@H:16]1[CH2:21][C@@H:20]2[C@@H:18]([CH2:19]2)[N:17]1[C:22](=[O:44])[CH2:23][N:24]1[C:32]2[C:27](=[CH:28][C:29]([OH:33])=[CH:30][CH:31]=2)[C:26]([C:41](=[O:43])[CH3:42])=[N:25]1)=[O:15]

Participants

4

Reactant 1

HCID 68283070(1R,3S,5R)-2-[2-(3-Acetyl-5-benzyloxy-indazol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoromethoxy-phenyl)-amide

Product 1

HCID 68283143(1R,3S,5R)-2-[2-(3-Acetyl-5-hydroxy-indazol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoromethoxy-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1R,3S,5R)-2-[2-(3-acetyl-5-benzyloxy-indazol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoromethoxy-phenyl)-amide (2.0 g, 3.28 mmol) and Pd/C (10%, 165 mg) in MeOH (40 mL) was stirred under a H2 atmosphere for 1 h. The mixture was filtered through a celite pad and concentrated. The product was used in the next step without further purification. MS (UPLC-MS): 521 [M+H]+; tR (HPLC conditions f): 2.02 min.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. concentrationconcentrated
  3. customThe product was used in the next step without further purification
  4. custom2.02 min.

Sources & evidence

ORD record
ord-2aa63269d59f4b55a598939dc3a9a72e
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…