HCID 59278135, compound → HCID 59278250, compound

HRID 1361131Notes

Reaction equation

HRID 1361131 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[C:10]([C@@H:12]([NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])[CH2:13][CH:14]=[CH2:15])[CH:9]=[CH:8][N:7]=1)(=[O:5])=[O:4])[CH3:2]>CO.[Pd]>[CH2:1]([S:3]([C:6]1[CH:11]=[C:10]([C@@H:12]([NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])[CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][N:7]=1)(=[O:4])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 59278135HCID 59278135, compound

Product 1

HCID 59278250HCID 59278250, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-ethanesulfonyl-pyridin-4-yl)-but-3-enyl]-amide (136 mg, 0.284 mmol) in MeOH (30 mL) was hydrogenated over 10% Pd/C using a continuous flow hydrogenation apparatus (conditions: full H2 mode, flow rate 1 mL/minute, 30° C., 1 atmosphere). The solution was concentrated in vacuo and purified by reversed-phase HPLC using a 20 minute gradient of 5-95% acetonitrile (0.1% TFA) in water (0.1% TFA) (flow rate=25 mL/min). The desired fractions were combined, neutralized with saturated aqueous sodium bicarbonate and extracted with dichloromethane (3×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford the title compound as an off white solid.

Workup

  1. customa continuous flow hydrogenation apparatus (conditions: full H2 mode, flow rate 1 mL/minute, 30° C., 1 atmosphere)
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified by reversed-phase
  4. extractionextracted with dichloromethane (3×20 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-221ce53378e04531bee4ec0bd0a421db
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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