HCID 68284157, compound → HCID 68284403, compound

HRID 1527591Notes

Reaction equation

HRID 1527591 reaction equation
C([O:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([C:43](=[O:45])[CH3:44])=[N:16][N:17]2[CH2:20][C:21]([N:23]2[CH2:27][C@H:26]([F:28])[C@@H:25]([O:29][CH3:30])[C@H:24]2[C:31](=[O:42])[NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[F:41])=[O:22])=[CH:13][CH:12]=1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:43]([C:15]1[C:14]2[C:18](=[CH:19][C:11]([C:9]([OH:10])=[O:8])=[CH:12][CH:13]=2)[N:17]([CH2:20][C:21]([N:23]2[CH2:27][C@H:26]([F:28])[C@@H:25]([O:29][CH3:30])[C@H:24]2[C:31](=[O:42])[NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[F:41])=[O:22])[N:16]=1)(=[O:45])[CH3:44]

Participants

4

Reactant 1

HCID 68284157HCID 68284157, compound

Product 1

HCID 68284403HCID 68284403, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Acetyl-1-{2-[(2S,3S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-3-methoxy-pyrrolidin-1-yl]-2-oxo-ethyl}-1H-indazole-6-carboxylic acid benzyl ester (47 mg, 0.063 mmol) was dissolved in MeOH (5 mL), Pd/C (10%, 5 mg) was added and the solution was degassed 3 times replacing air by nitrogen and finally nitrogen by hydrogen. The reaction mixture was further stirred under hydrogen atmosphere for 1 h. The catalyst was removed through a pad of Celite and washed with MeOH. The solvent was concentrated under reduced pressure and the crude residue was purified by preparative HPLC (Waters Sunfire C18-ODB, 5 μm, 30×100 mm, eluent: 5% to 100% CH3CN in H2O in 25 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min). MS (LC/MS): 549.5 [M+H]+; 547.5 [M−H]−; tR (HPLC conditions f): 1.93 min.

Workup

  1. customthe solution was degassed 3 times
  2. customThe catalyst was removed through a pad of Celite
  3. washwashed with MeOH
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe crude residue was purified by preparative HPLC (Waters Sunfire C18-ODB, 5 μm, 30×100 mm, eluent: 5% to 100% CH3CN in H2O in 25 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min)
  6. custom1.93 min.

Sources & evidence

ORD record
ord-540c44c930b14efcbf53ea519dd15c6e
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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