Lithium borohydride → HCID 44468308, compound

HRID 2382943Notes

Reaction equation

HRID 2382943 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:21]=[N:22][N:23]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:24]=3[CH:25]=[CH:26][CH:27]=2)=[O:18])=[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[N:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:21]=[N:22][N:23]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[C:24]=3[CH:25]=[CH:26][CH:27]=2)=[O:18])=[CH:13][CH:14]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58138801HCID 58138801, compound

Product 1

HCID 44468308HCID 44468308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 3-[5-({[1-(4-fluoro-phenyl)-1H-indazole-4-carbonyl]-amino}-methyl)-pyridine-2-sulfonyl]-propionic acid methyl ester (33 mg, 0.066 mmol) in THF (5 mL) was treated with lithium borohydride (8.7 mg, 0.40 mmol) at room temperature and the mixture was warmed at reflux. After 1 hour, the reaction was cooled to room temperature, quenched with water (50 mL) and diluted with ethyl acetate (50 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in CH2Cl2 to afford the title compound.

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux
  3. customquenched with water (50 mL)
  4. additiondiluted with ethyl acetate (50 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (2×25 mL)
  7. washThe combined organic layers were washed with brine (20 mL)
  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

Sources & evidence

ORD record
ord-f2a5d02e81d541b2ad61c5ae14fdeaa0
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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