HCID 117889587, compound → HCID 117892033, compound

HRID 930536Notes

Reaction equation

HRID 930536 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:18]=[C:19]([NH:25][CH:26]=O)[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:18]=[C:19]([NH:25][CH3:26])[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 117889587HCID 117889587, compound

Product 1

HCID 117892033HCID 117892033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[5-(1-Benzyl-1H-benzoimidazol-2-yl)-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl]-formamide G1 (93.000 mg; 0.259 mmol) is suspended in THF (extra dry, 2.000 ml), borane-tetrahydrofuran complex (0.259 ml; 0.259 mmol) is added at 0° C. under argon. After 1 h stirring at RT, a second portion of borane-tetrahydrofuran complex (0.259 ml; 0.259 mmol) is added to the reaction mixture at 0° C. After an extra 1 h stirring at RT, a final third portion of borane-tetrahydrofuran complex (0.259 ml; 0.259 mmol) is added to the reaction mixture at 0° C. The mixture is stirred for 30 min at RT. The reaction mixture is quenched with water and extracted with 3×10 ml DCM. The combined organic layer is dried with Na2SO4, filtered and concentrated under reduced pressure. The residue is purified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: cyclohexane/EtOAc=100%/0% to 0%/100%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm). Product containing fractions are combined and concentrated under reduce pressure.

Workup

  1. additionborane-tetrahydrofuran complex (0.259 ml; 0.259 mmol) is added at 0° C. under argon
  2. additiona second portion of borane-tetrahydrofuran complex (0.259 ml; 0.259 mmol) is added to the reaction mixture at 0° C
  3. stirringAfter an extra 1 h stirring at RT
  4. additiona final third portion of borane-tetrahydrofuran complex (0.259 ml; 0.259 mmol) is added to the reaction mixture at 0° C
  5. stirringThe mixture is stirred for 30 min at RT
  6. customThe reaction mixture is quenched with water
  7. extractionextracted with 3×10 ml DCM
  8. dry with materialThe combined organic layer is dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: cyclohexane/EtOAc=100%/0% to 0%/100%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm)
  12. additionProduct containing fractions
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-8cc9d15dbe924654896db519160eb478
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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