Sodium borohydride → HCID 66701633, compound

HRID 1186766Notes

Reaction equation

HRID 1186766 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][C:4]([NH:10][S:11]([C:14]2([CH2:17][CH:18]=[O:19])[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[C:3]1[N:20]([C:28]1[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=1[F:35])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].[BH4-].[Na+]>CO>[F:35][C:29]1[CH:30]=[C:31]([I:34])[CH:32]=[CH:33][C:28]=1[N:20]([C:3]1[N:2]([CH3:1])[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][C:4]=1[NH:10][S:11]([C:14]1([CH2:17][CH2:18][OH:19])[CH2:16][CH2:15]1)(=[O:13])=[O:12])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86664506HCID 86664506, compound

Product 1

HCID 66701633HCID 66701633, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [1,5-dimethyl-6-oxo-3-({[1-(2-oxoethyl)cyclopropyl]sulfonyl}amino)-1,6-dihydropyridin-2-yl](2-fluoro-4-iodophenyl)carbamate (304 mg, 0.491 mmol) in MeOH (6 ml) at 0° C. under a nitrogen atmosphere was added NaBH4 (4 eq, 74 mg, 1.963 mmol). The reaction mixture was stirred at this temperature for 1 hour and then allowed to warm up to room temperature. The solvent was removed under reduced pressure, the residue partitioned between ethyl acetate (10 ml), H2O (5 ml) and 1N aq HCl (5 ml). The aqueous phase was separated and extracted twice with ethyl acetate (10 ml). The combined organic layers were washed with brine (20 ml), dried (silicone filter) and concentrated under reduced pressure. The crude material was purified by flash chromatography (Biotage system) to afford the title compound (321 mg, quant.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate (10 ml), H2O (5 ml) and 1N aq HCl (5 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted twice with ethyl acetate (10 ml)
  5. washThe combined organic layers were washed with brine (20 ml)
  6. customdried
  7. filtration(silicone filter)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by flash chromatography (Biotage system)

Sources & evidence

ORD record
ord-ade409a6febf4c8bb8c74056ea336378
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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