Formaldehyde → HCID 44181677, compound

HRID 415337Notes

Reaction equation

HRID 415337 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([C:13]3[CH:32]=[CH:31][C:16]([CH2:17][CH2:18][N:19]([CH3:30])[C:20](=O)OCC4C=CC=CC=4)=[CH:15][CH:14]=3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].C=O.[H][H]>CO.[Pd]>[CH3:30][N:19]([CH3:20])[CH2:18][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[O:11][C:12]3[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=[CH:7][C:8]=3[N:9]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 66621653HCID 66621653, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181677HCID 44181677, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)phenethyl(methyl)carbamate (30 mg, 0.069 mmol), paraformaldehyde (4 mg, 0.14 mmol), and 10% Pd/C (10 mg) in methanol (10 ml) was stirred at room temperature over 1 atm of hydrogen for 4 h. Then the mixture solution was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by prep-HPLC to obtain 2-(4-(2-(dimethylamino)ethyl)phenyl)benzo[d]oxazole-7-carboxamide (10 mg, yield 48%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 2.34 (s, 6H), 2.62-2.66 (m, 2H), 2.89-2.93 (m, 2H), 7.46-7.52 (m, 3 H), 7.88-7.91 (m, 2H), 8.224-8.26 (d, J=8.4 Hz, 2H). LC-MS (ESI) m/z: 310 (M+1)+.

Workup

  1. filtrationThen the mixture solution was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-7d1008830274404a848925aab85672c7
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…