Ethanol → 5-{5-[(Benzyl-ethyl-amino)-methyl]-pyridin-3-yl}-3-methyl-3H-benzooxazol-2-one

HRID 1253922Notes

Reaction equation

HRID 1253922 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[CH:18][C:19]3[O:23][C:22](=[O:24])[N:21]([CH3:25])[C:20]=3[CH:26]=2)[CH:13]=[N:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27](O)[CH3:28]>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([N:8]([CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[CH:18][C:19]3[O:23][C:22](=[O:24])[N:21]([CH3:25])[C:20]=3[CH:26]=2)[CH:13]=[N:14][CH:15]=1)[CH2:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 667979925-[5-(Benzylamino-methyl)-pyridin-3-yl]-3-methyl-3H-benzooxazol-2-one

Product 1

HCID 498020185-{5-[(Benzyl-ethyl-amino)-methyl]-pyridin-3-yl}-3-methyl-3H-benzooxazol-2-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 5-(5-(Benzylamino-methyl)-pyridin-3-yl)-3-methyl-3H-benzooxazol-2-one (crude from step 2, ˜0.39 mmol) and Pd(OH)2 (20 mg, 10%) in ethanol (10 mL) and acetic acid (0.5 mL) was stirred under 1 atmosphere of H2 at room temperature for 48 h. After filteration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-5%) and yielded yellow solid (3 mg), ESI-MS m/z: 387.9 [M+1]+, Retention time 1.45 min; 1HNMR (CDCl3, 400.342 MHz) δ 1.48 (t, J=7.2 Hz, 3H), 3.05 (s, 2H), 3.48 (s, 3H), 4.23 (s, 2H), 4.05-4.27 (m, 2H), 7.21 (s, 1H), 7.23 (5, 1H), 7.40-7.43 (m, 3H), 7.62-7.64 (m, 2H), 7.83 (s, 1H), 8.52 (5, 1H), 8.85 (d. J=1.84 Hz, 1H), 9.21 (s, 1H).

Workup

  1. concentrationAfter filteration and concentration
  2. customthe residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-5%)

Sources & evidence

ORD record
ord-47dc2f3b3c764959966306b0fe987d29
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

Loading…