Acetic Acid → 5-[5-(Benzylamino-methyl)-pyridin-3-yl]-3-methyl-3H-benzooxazol-2-one

HRID 1253921Notes

Reaction equation

HRID 1253921 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:17]=O)[CH:14]=[N:15][CH:16]=3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:19].[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:20]([NH:27][CH2:17][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[O:4][C:3](=[O:19])[N:2]([CH3:1])[C:6]=3[CH:7]=2)[CH:16]=[N:15][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866633595-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde

Product 1

HCID 667979925-[5-(Benzylamino-methyl)-pyridin-3-yl]-3-methyl-3H-benzooxazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde (100 mg, 0.39 mmol), Benzylamine (46.4 mg, 0.43 mmol), acetic acid (50 uL) and sodium triacetoxyborohydride (25 0 mg, 1.18 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 2 h. The mixture was quenched with NaHCO3 (saturated solution) and extracted with CH2Cl2 (20 mL×3). The combined extracts were washed with brine and dried over anhydrous Na2SO4. After filtration and concentration, the residue was obtained as yellow solid. ESI-MS m/z: 346.1 [M+1]+, Retention time 1.11 min.

Workup

  1. customThe mixture was quenched with NaHCO3 (saturated solution)
  2. extractionextracted with CH2Cl2 (20 mL×3)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was obtained as yellow solid

Sources & evidence

ORD record
ord-a0908c60216246c391c83f5fe32a1f6c
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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