Sodium borohydride → 6-Chloro-2-(3-hydroxy-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide

HRID 1056791Notes

Reaction equation

HRID 1056791 reaction equation
[F:1][C:2]1([F:29])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:27][CH2:26][C:25](=[O:28])[CH2:24]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1.[BH4-].[Na+]>C1COCC1>[F:29][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1185696266-Chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide

Product 1

HCID 1185666256-Chloro-2-(3-hydroxy-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide (30 mg, 0.07 mmol, 1.00 eq) in dry THF (3 mL) was added NaBH4 (5.34 mg, 0.14 mmol, 2.00 eq) at 0° C. and left to stir at RT for 1 h. The reaction mixture was quenched with water (5 mL) and extracted with EtOAc (15 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford crude product which was purified using preparative HPLC to afford the title compound as (10.00 mg, 0.02 mmol, 32.9%) off-white gum. 1H NMR (400 MHz, DMSO-d6): δ 8.26-8.39 (bs, 1H), 7.98-8.20 (m, 1H), 7.53-7.72 (m, 2H), 6.53-6.71 (m, 1H), 4.42 (d, J=5.52 Hz, 1H), 3.70 (d, J=3.83 Hz, 1H), 3.48-3.51 (m, 2H), 2.08-2.37 (m, 6H), 1.69-2.05 (m, 8H), 1.26-1.49 (m, 2H). m/z: 423 [M+H]+

Workup

  1. waitleft
  2. customThe reaction mixture was quenched with water (5 mL)
  3. extractionextracted with EtOAc (15 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product which
  9. customwas purified

Sources & evidence

ORD record
ord-b3ebcbc9d58d4b39b5ee6f13567c44b3
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

Loading…