Sodium borohydride → 1-(2-Hydroxy-ethyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

HRID 1259392Notes

Reaction equation

HRID 1259392 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[C:13]([NH:23][S:24]([C:27]2([CH2:30][CH:31]=[O:32])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[C:14]2[O:22][CH2:21][CH2:20][N:15]2[C:16](=[O:19])[C:17]=1[CH3:18]>C1COCC1.CO.C(Cl)Cl>[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[C:13]([NH:23][S:24]([C:27]2([CH2:30][CH2:31][OH:32])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[C:14]2[O:22][CH2:21][CH2:20][N:15]2[C:16](=[O:19])[C:17]=1[CH3:18]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 583805691-(2-Oxo-ethyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

Product 1

HCID 529340931-(2-Hydroxy-ethyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amideYield 60.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.1 g, 2.6 mmol) was added to a stirred solution of 1-(2-Oxo-ethyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide (0.12 g, 0.21 mmol) in THF (5 mL) and MeOH (2 mL) at room temperature. The resulting mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC (10% MeOH in DCM). The reaction mixture was concentrated under reduced pressure and partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried over Na2SO4, filtered and the filtrate was concentrated. Purification by column chromatography on silica gel (2-4% MeOH in DCM) afforded 70 mg of the product (58% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between ethylacetate and water
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customPurification by column chromatography on silica gel (2-4% MeOH in DCM)

Sources & evidence

ORD record
ord-9b35209dc8484e1ab4cc679c1cc94bd3
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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