Lithium borohydride → HCID 45138463, compound

HRID 559629Notes

Reaction equation

HRID 559629 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][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])[CH:12]=[CH:11][N:10]=1)(=[O:8])=[O:7].[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])[CH:12]=[CH:11][N:10]=1)(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 59278102HCID 59278102, compound

Product 1

HCID 45138463HCID 45138463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 3-[4-({[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-methyl)-pyridine-2-sulfonyl]-propionic acid methyl ester (33 mg, 0.066 mmol) in THF (5 mL) was added lithium borohydride (8.6 mg, 0.40 mmol). The mixture was then warmed at reflux. After 1 hour, the reaction was cooled to room temperature, quenched with water (50 mL) and diluted with EtOAc (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in CH2Cl2. The residue was further purified by reversed-phase HPLC. The desired fractions were combined and lyophilized to afford the title compound as a yellow solid.

Workup

  1. temperatureThe mixture was then warmed
  2. temperatureat reflux
  3. customquenched with water (50 mL)
  4. additiondiluted with EtOAc (50 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with EtOAc (2×25 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography
  12. washeluting with a gradient of 0-10% MeOH in CH2Cl2
  13. customThe residue was further purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-f3fff2056049416b82b999d99fb7553b
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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